ЗАМЕЩЕННЫЕ ФЕРРОЦЕНИЛДИФОСФИНЫ В КАЧЕСТВЕ ЛИГАНДОВ ДЛЯ ГОМОГЕННЫХ КАТАЛИЗАТОРОВ ГИДРИРОВАНИЯ

Описаны соединения формулы I, ! , ! где R1 представляет собой фенил, R2 представляет собой диметиламиногруппу, и R представляет собой радикал формулы ! , ! где R3 представляет собой метил, R4 представляет собой Н или метоксил, которые являются лигандами для металлокомплексов, используемых как гомогенные катализаторы гидрирования прохиральных органических соединений, содержащих двойные связи, при использовании которых можно достичь очень высоких активности и производительности, а также энантиоселективности. 4 н. и 2 з.п. ф-лы.

АСИММЕТРИЧНАЯ ВСПОМОГАТЕЛЬНАЯ ГРУППА

Изобретение относится к хиральному реагенту формулы (I') для получения производного нуклеозид 3'-фосфорамидита формул (Va') или (Vb'), которые могут использоваться в химической промышленности для синтеза олигонуклеотидов:где Gпредставляет собой H или группу формулы (II), Gпредставляет собой группу формул (III) или (V), или Gи Gвместе образуют группу формулы (IV),,,,,где G- Gпредставляют собой H или нитрогруппу, G- Gпредставляют собой Салкил или Сарил, G- Gпредставляют собой Н, G- Gпредставляют собой H или Салкил. Предложены новые реагенты и полученные с их использованием новые производные нуклеозид 3'-фосфорамидита формул (Va') или (Vb'), эффективные для синтеза олигонуклеотидов,,,где Gпредставляет собой 4,4'-диметокситритил, Rпредставляет собой Н, О-Салкил, галоген, Rпредставляет собой -СН-, и Bs выбран из остатков немодифицированных и модифицированных нуклеозидов. Предложены новые эффективные способы синтеза указанных производных олигонуклеотидов. 6 н. и 8 з.п. ф-лы, 69 пр., 1 табл., ...

СТЕРЕОИЗОМЕРНО ОБОГАЩЕННЫЕ 3-АМИНОКАРБОНИЛЬНЫЕ БИЦИКЛОГЕПТЕНОВЫЕ ПИРИМИНДИАМИНЫ И ИХ ПРИМЕНЕНИЯ

... 1. Соединение структурной формулы (I)включая его пролекарства, соли, гидраты, сольваты и N-оксиды, которое обогащено соответствующим диастереомером структурной формулы (Ia)где каждый Rявляется независимо выбранным из группы, состоящей из атома водорода, низшего алкила, -(CH)OH, -OR, -O(CH)-R, -O(CH)-R, -C(O)OR, атома галогена, -CFи -OCF;каждый Rявляется независимо выбранным из группы, состоящей из атома водорода, низшего алкила, -OR, -O(CH)-R, -O(CH)-R, -NHC(O)R, атома галогена, -CF, -OCF,;каждый Rявляется независимо выбранным из группы, состоящей из атома водорода, низшего алкила, -(CH)-OH, -OR, -O(CH)-R, -O(CH)-R, атома галогена, -CF, -OCF,;каждый Rявляется независимо выбранным из группы, состоящей из атома водорода, низшего алкила, арилалкила, -OR, -NRR, -C(O)R, -C(O)ORи -C(O)NRR;Rпредставляет собой атом водорода, атом галогена, атом фтора, -CN, -NO, -C(O)ORили -CF;n каждое независимо представляет собой целое число от 1 до 3;каждый Rявляется независимо выбранным из группы, состоящей ...

СПОСОБ ПОЛУЧЕНИЯ ОПТИЧЕСКИ АКТИВНОГО СОЕДИНЕНИЯ ОКСИДА ХРОМЕНА

... 1. Способ получения оптически активного соединения оксида хромена, представленного формулой (14), формулой (15), формулой (16) или формулой (17): ! ! (где R5, R6, R7, R8, R9, R10, А, W, X, Y и Z являются такими, как описано ниже, а абсолютная конфигурация атомов углерода, обозначенных *, означает (R) или (S)), где указанный способ включает: ! асимметрическое эпоксидирование соединения хромена, представленного формулой (10), формулой (11), формулой (12) или формулой (13), с окислителем в растворителе; ! ! (где каждый из R5, R6, R7 и R8 в формуле (10) независимо представляет собой атом водорода, цианогруппу, нитрогруппу, атом галогена, С1-4алкильную группу (алкильная группа может быть необязательно замещена атомом галогена, гидроксигруппой, цианогруппой, нитрогруппой, С1-4алкоксигруппой, С1-4алкилкарбонилоксигруппой, С1-4алкилкарбониламиногруппой или С1-4алкоксикарбонильной группой (алкоксигруппа, алкилкарбонилоксигруппа, алкилкарбониламиногруппа и алкоксикарбонильная группа могут быть необязательно ...

СПОСОБ ПОЛУЧЕНИЯ 5R-[(БЕНЗИЛОКСИ)АМИНО]ПИПЕРИДИН-2S-КАРБОНОВОЙ КИСЛОТЫ ИЛИ ЕЁ ПРОИЗВОДНОГО

Настоящая заявка относится к способам получения 5R-[(бензилокси)амино]пиперидин-2S-карбоновой кислоты или ее производных безвредным для окружающей среды путем. В способе применяют L-глутаминовую кислоту в качестве исходного вещества, причем ее сначала подвергают реакции эстерификации в присутствии кислотного реагента, а затем последовательно осуществляют реакцию с 2-галогенацетатом и средством для введения защитной группы для атома N или со средством для введения защитной группы для атома N и 2-галогенацетатом в основных условиях с получением соединения IV; затем полученное соединение IV подвергают внутримолекулярной конденсации с образованием кольца при воздействии сильного основания с получением защитная-группа-для-атома-пиперидин-5-он-2S-карбоксилата (V). Полученное соединение V применяют для получения 5R-[(бензилокси)амино]пиперидин-2S-карбоновой кислоты (или ее сложного эфира) посредством одного из нижеследующих путей. Путь 1: соединение V подвергают удалению защитной группы, конденсации ...

СПОСОБ ПОЛУЧЕНИЯ СОЕДИНЕНИЯ ПИРАЗОЛАМИДА

АСИММЕТРИЧЕСКИЙ СИНТЕЗ ЗАМЕЩЕННОГО ПИРРОЛИДИН-2-КАРБОКСАМИДА

СПОСОБ ПОЛУЧЕНИЯ ЭНАНТИОМЕРНО ЧИСТЫХ (S)-АМИНОКИСЛОТ НА ОСНОВЕ КОМПЛЕКСА [(S)-BPB-GLY] NI(II), НАПРЯМУЮ СВЯЗАННЫХ С ФУЛЛЕРЕНОВЫМ ЯДРОМ ЧЕРЕЗ α-УГЛЕРОДНЫЙ АТОМ, В ФОРМЕ ХИРАЛЬНЫХ (f,tA) И (f,tC) 1,4-АДДУКТОВФУЛЛЕРЕНА

СПОСОБ ПОЛУЧЕНИЯ И ВЫДЕЛЕНИЯ 2-АЦИЛАМИНО-3-ДИФЕНИЛПРОПИОНОВОЙ КИСЛОТЫ

... 1. Способ получения соединения формулы (III) или его соли,в котором R1 представляет собой (C-C)алкил, такой как метил или этил, или представляет собой замещенный или незамещенный (C-C)арил, такой как фенил или пара-хлорфенил, включающий превращение соединения формулы (IV) или его солив котором R1 отвечает определениям, приведенным для соединения формулы (III), в условиях, обеспечивающих протекание декарбоксилирования, с целью получения соединения формулы (III).2. Способ по п.1, в котором условия, обеспечивающие протекание декарбоксилирования, достигаются путем нагревания до температуры от 80°C до 250°C.3. Способ получения хирального соединения формулы (II),в которомR1 представляет собой (C-C)алкил, такой как метил или этил, или замещенный или незамещенный (C-C)арил, такой как фенил или пара-хлорфенил,R2 представляет собой (C-C)алкил, такой как метил, или представляет собой остаток R3R4NC(=O)- или R5OC(=O)-, в котором R3 и R4 независимо выбраны из водорода или (C-C)алкила, a R5 представляет ...

СПОСОБ ПОЛУЧЕНИЯ СОЕДИНЕНИЯ, СОЕДИНЕНИЯ, КОМПЛЕКСНЫЙ МЕТАЛЛООРГАНИЧЕСКИЙ КАТАЛИЗАТОР

... 1. Способ получения соединения формулы (I)в которой R1 и R2 могут быть одинаковыми или различными и по отдельности представляют собой замещенную или незамещенную группу, выбранную из алкильной, циклоалкильной, арильной, алкилокси-, циклоалкилокси-, арилокси, алкиламино-, циклоалкиламино, ариламино, металлоценильной группы;R3, R4, R5, R6 могут быть одинаковыми или различными и по отдельности представляют собой атом водорода либо замещенную или незамещенную группу, выбранную из алкильной, циклоалкильной, арильной, алкилокси-, циклоалкилокси-, арилокси-, алкиламино-, циклоалкиламино-, ариламиногруппы;Е представляет собой замещенную или незамещенную группу, выбранную из PR7R8, P(BH)R7R8, -CH-PR7R8, -CH-P(BH)R7R8, -BR9R10, -CR11R12OH, -COR11, -SiR11R12R13; -SiR11R12-CH-PR7R8;где R7 и R8 могут быть одинаковыми или различными и по отдельности представляют собой водород, замещенную или незамещенную группу, выбранную из алкильной, циклоалкильной, арильной, алкилокси-, циклоалкилокси-, арилокси, ...

ЗАМЕЩЕННЫЕ ФЕРРОЦЕНИЛДИФОСФИНЫ В КАЧЕСТВЕ ЛИГАНДОВ ДЛЯ ГОМОГЕННЫХ КАТАЛИЗАТОРОВ ГИДРИРОВАНИЯ

... 1. Соединение формулы I в виде практически чистых энантиомеров, где R1 представляет собой С1-С4алкил, С6-С10арил или С7-С11аралкил, R2 представляет собой нециклическую или циклическую вторичную аминогруппу, R представляет собой радикал формулы где R3 представляет собой С1-С4алкил или С1-С4алкоксил, и R4 представляет собой Н, С1 -С4алкил или С1-С4алкоксил. 2. Соединение по п.1, где R1 в соединении формулы I представляет собой фенил. 3. Соединение по п.1, где нециклическая вторичная аминогруппа R2 соответствует формуле R5R6N-, где R5 и R6 представляют собой независимо друг от друга C1 -С6алкил, С3-С8циклоалкил, С6-С10арил, или С7-С11аралкил, где циклоалкильные группы и арильные группы являются незамещенными, или замещенными С1-С4алкилом или С1-С4алкоксилом, или R5 и R6 вместе образуют тетраметилен, пентаметилен или 3-оксапентилен. 4. Соединение по п.3, где каждый из R5 и R6 представляет собой метил. 5. Соединение по п.1, где оба радикала R3 представляют собой метил, трет-бутил или метоксил ...

OPTISCH AKTIVE DIPHOSPHINE UND HERSTELLUNGSVERFAHREN DURCH AUFTRENNUNG DER RACEMATMISCHUNG

Verwendung von molekulargewichtsvergrößerten Katalysatoren in einem Verfahren zur asymmetrischen kontinuierlichen Hydrierung, neue molekulargewichtsvergrößerte Liganden und Katalysatoren

Die vorliegende Erfindung richtet sich auf eine Verwendung von molekulargewichtsvergrößerter homogen löslicher Katalysatoren Verfahren zur asymmetrischen kontinuierlichen Hydrierung von C=C-, C=N- oder C=O-Doppelbindungen mittels molekulargewichtsvergrößerter homogen löslicher Katalysatoren in einem Membranreaktor. DOLLAR A Bisherige im Stand der Technik vorgeschlagene Hydrierverfahren liefen diskontinuierlich ab. Die kontinuierliche Fahrweise hilft dagegen Prozeßkosten zu sparen. DOLLAR A Angegeben werden auch neue molekulargewichtsvergrößerte Liganden und Katalysatoren.

Chirale Diphosphin-Verbindung, Zwischenprodukte zu ihrer Herstellung, Übergangsmetall-Komplexe davon und asymmetrischer Hydrierungskatalysator

Synthesis of chiral cyanohydrins

Novel metallocene-based phosphorus chiral phosphines

ACID ADDITION SALTS OF D-(+)-1-(3-HYDROXYPHENYL)-2-AMINOPROPANE AND THEIR MANUFACTURE AND USE

Physiologically tolerated acid addition salts of D-(+)-1-(3-hydroxyphenyl)-2-aminopropane with optically active acids are prepared. These salts are obtained by resolving racemic 1-(3-hydroxyphenyl)-2-aminopropane by the action of an acid with the L configuration. The salts can be used for the treatment of hypotensive circulatory states.

Process

A metallocenyl compound for formula (I) wherein Ra, Rb, Rc and Rd are independently selected from substituted or unsubstituted C1-C20-alkyl, C3-C15-cycloalkyl, C5-C20-aryl and C4-C20-heteroaryl, wherein the heteroatom of the heteroaryl ring are selected from sulfur, oxygen and nitrogen; Re and Rf are independently selected from the group consisting of substituted or unsubstituted C1-C20-alkyl, C3-C15-cycloalkyl and C5-C20-aryl; M is selected from Fe, Ru, Os and Ni; m is an integer from 0 to 4; j is 0 or 1; and when j = 0, n is an integer from 0 to 5 and k is 1 or 2; when j = 1, n is an integer from 0 to 4 and k is 1; Y is (j+1)Zk- or Z(j+1)k-; Z is a non optically active anion; * denotes a chiral atom. A process for the preparation of a metallocenyl compound of formula (I) comprising mixing a compound of formula (II) with an acid Hk(j+1)Z in a solvent. A process of increasing the optical purity of a compound of formula (II). A process for the asymmetric transfer hydrogenation of a metallocenyl ...

Pyrimidinyl-piperazines useful as dopamine D3/D2 receptor ligands

Homogeneous oxidation catalysis using metal complexes.

The present method provides a method of transferring oxygent to at least one oxidizable site on a target compound. The method includes the steps of selectively oxidizing an oxidizable site on a target compound by reacting in solution; the target compound, a source of oxygen atoms, a source of a lewis acid, such as a proton, alkali, alkaline earth, rare earth, transition metal or main group metal ion, and a catalyst. The catalyst has general structure (i)wherein z is preferably n, but may include o and mo is a transition metal-oxo species. The lewis acid binds to a bidentate secondary site on the ch1 substituent to form a lewis acid-catalyst complex.

Pyrimidinyl-piperazines useful as dopamine d3/d2 receptor ligands

Homogeneous oxidation catalysis using metal complexes

Asymmetric syntheses.

PROCEDURE FOR THE CATALYTIC HYDROGENATION OF CARBON HETERO ATOMIC DOUBLE BONDS

PROCEDURE FOR THE PRODUCTION OF OPTICALLY ACTIVE ALCOHOL IN PRESENCE OF RHODIUM, A CHIRALEN FERROCENYLDIPHOSPHIN AND AN OPTICALLY ACTIVE DIAMINE

PHOSPHINVERBINDUNGEN, ÜBERGANGSMETALLKOMLEXE WITH THE CONNECTIONS, WHICH WHEN LIGAND IN IT CONTAINING ARE, AND ASYMMETRICAL SYNTHESIS CATALYSTS WITH THESE COMPLEXES

BISPHOSPHINE AS BIDENTAT LIGANDS

PROCEDURE FOR THE PRODUCTION OF AN OPTICALLY ACTIVE NITRO COMPOUND

PROCEDURE FOR THE ASYMMETRICAL SYNTHESIS

HYDROGENATION CATALYSTS

PROCEDURE FOR THE PRODUCTION OPTICAL OF ACTIVE CARBONYLVERBINDUNGEN

PROCEDURE FOR THE PRODUCTION OF CHIRALER OF SUBSTITUTED DIOLE AND DIOLANALOGER DERIVATIVES

CATALYSTS ON BASIS FROM COPPER COMPLEXES TO THE SYNTHESIS OF OPTICALLY ACTIVE CHRYSANTHEMSÄURE

RUTHENIUM COMPLEXES OF PHOSPHINAMINOPHOSPHINLIGANDEN

PROCEDURE FOR THE PRODUCTION OPTICAL OF ACTIVE ALPHAALKYLCARBONYLVERBINDUNGEN

PROCEDURE FOR ENANTIOSELEKTIVEN THE HYDROGENATION THE CARBONYLGRUPPE USING RUTHENIUM COMPLEXES WITH BIPHOSPHINELIGANDEN

PROCEDURE FOR THE PRODUCTION OF HIGH ENANTIOMERENREINEN DIFUNKTIONELLEN CONNECTIONS

ACETYL NICHE SULFONAMID THIOL TACE INHIBITORS

PROCEDURE FOR the PRODUCTION OF 3-FLUOR-D-ALANIN

PROCEDURE FOR THE PRODUCTION OF OPTICALLY ACTIVE ONES ALPHA AMINOSAUREN AND YOUR ESTERS AND/OR SALTS

CHIRALE LIGANDS, ITS TRANSITION METAL COMPLEXES AND THE APPLICATION OF THESE IN ASYMMETRICAL REACTIONS

LIGAND AND THEIR USE

CHIRALE FERROCENE

RACEMISIERUNGSVERFAHREN WITH THE PRODUCTION OF LEVOBUPIVACAINE AND SIMILAR ONES

PROCEDURE FOR THE PRODUCTION OF ORGANOZINKREAGENZIEN

HETERO ARYL ARYL DIPHOSPHINE AS CHIRALE LIGAND

CATALYTIC COMPOSITION AND PROCEDURE FOR ASYMMETRICAL ALLYLI ALKYLATION

CHIRALER FIRM CATALYST, ITS PRODUCTION AND ITS USE TO HESRTELLUNG OF PRACTICAL ENANTIOMERENREINEN PRODUCTS

NEW ASYMMETRICAL PHOSPHIN LIGAND

NEW DIARSINVERBINDUNGEN

ALLYLI SUBSTITUTING REACTIONS

IMPROVEMENT ENANTIOSELEKTIVITÄT WHEN REDUCTIONS WITH BORANREAGENZIEN

CHIRALE CATALYSTS FOR THE ASYMMETRICAL ACYLATION AND USED TRANSFORMATIONS

3,5-DIOXO-8-AZA-TRICYCLO (5.2.1.00, 0) DECANE-9 of METHANOLS, YOUR METAL COMPLEXES AND YOUR USE FOR ENANTIOSELEKTIVEN HYDROGENATION

BY TRANSITION METAL COMPLEXES WITH CYCLIC CHIRALEN ASYMMETRICAL SYNTHESIS CATALYZED LIGANDS

PROCEDURE FOR THE PRODUCTION OF OPTICALLY ACTIVE CARBONIC ACIDS

Production method for pyrazole-amide compound

The present invention is a production method for a compound represented by formula [I] or a pharmaceutically acceptable salt thereof, or a hydrate of said compound or salt.

Stereoselective ring opening reactions

Use of molecularly imprinted polymers for stereo- and/or regioselective synthesis

Diphosphines, preparation and uses thereof

A process and an apparatus for producing episesamin-rich compositions

It is intended to provide a method and an apparatus for producing a composition containing episesamin at a concentration exceeding 50% by weight based on the total weight of sesamin and episesamin simply and in high yield. The method for producing a composition containing episesamin at a concentration exceeding 50% by weight simply and in high yield comprising the steps of converting at least a part of sesamin into episesamin by subjecting sesamin or a composition containing sesamin to epimerization and selectively crystallizing episesamin using the recrystallization method and the apparatus therefor are provided.

ENANTIOSELECTIVE AMINATION AND ETHERIFICATION___________________

MIXTURES OF CHIRAL MONOPHOSPHORUS COMPOUNDS USED AS LIGAND SYSTEMS FOR ASYMMETRIC TRANSITION METAL CATALYSIS

Method for producing (Z)-1-phenyl-1-diethylaminocarbonyl-2-hydroxymethyl cyclopropane

Improved method for producing intermediates for the production of macrocycles that are inhibitors of the proteasomic degradation of p27, such as argyrin and derivatives thereof

The present invention relates to an improved method for the synthesis of particular macrocycles that are inhibitors of the proteasomic degradation of p27, in particular argyrin and derivatives thereof.

6,6'-bis-(1-phosphanorbornadiene) diphosphines

Catalyst for asymmetric transfer hydrogenation

Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids

Ruthenium complexes and their use in asymmetric hydrogenation

Method for producing endo-9-azabicyclo[3.3.1]nonane-3-ol derivative

Provided is a method that makes it possible to obtain an endo-9-azabicyclo[3.3.1]nonane-3-ol derivative that is useful as an intermediate of agricultural and horticultural chemicals or pharmaceuticals at a low cost by reacting a 9-azabicyclo[3.3.1]nonane-3-on derivative with hydrogen under the presence of a catalyst comprising a ruthenium complex.

Modulators of the prostacyclin (PGI2) receptor useful for the treatment of disorders related thereto

Compounds having muscarinic receptor antagonist and beta2 adrenergic receptor agonist activity

The present invention relates to compounds acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients.

Picolinamides as fungicides

This disclosure relates to picolinamides of Formula (I) and their use as fungicides.

Method for producing glyco-conjugates of 20(s)-camptothecin

Acid addition salts of imidazolidinones as reaction catalysts

Chiral diphosphines and their metal complexes

Chiral phosphorated ligands useful in catalysts

Kinetic resolution of olefins

PROCESS FOR TRANSITION METAL-CATALYZED ASYMMETRIC HYDROGENATION OF ACRYLIC ACID DERIVATIVES, AND A NOVEL CATALYST SYSTEM FOR ASYMMETRIC TRANSITION METAL CATALYSIS

MONOPHOSPHINE COMPOUNDS, TRANSITION METAL COMPLEXES THEREOF AND PRODUCTION OF OPTICALLY ACTIVE COMPOUNDS USING THE COMPLEXES AS ASYMMETRIC CATALYSTS

P-CHIRAL PHOSPHOLANES AND PHOSPHOCYCLIC COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYTIC REACTIONS

Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrigenation, hydride transfer, allylic alkylation, hydrosilytation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation. Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.

CHIRAL LIGANDS FOR ASYMMETRIC CATALYSIS

An enantiomerically enriched compound of formula (4) or the opposite enantiomer thereof, wherein R is C1-10 alkyl. This compound, in the form of a transition metal complex, is useful as a catalyst for stereoselective hydrogenation.

POLYMERIC DIPHOSPHINE LIGANDS FOR HOMOGENEOUSLY SOLUBLE HYDROGENATION CATALYSTS, PROCESS FOR THE PRODUCTION THEROF AND USE

Molecular weight-enlarged, homogeneously soluble ligands for hydrogenation catalysts comprising homochiral active centres of bis(3,4-diarylphosphinyl)pyrrolidines. Once transferred into catalysts, the ligands may advantageously be used in membrane reactors in semi- continuous or continuous organic syntheses. Process and use, catalysts.

CHIRAL LIGANDS, TRANSITION-METAL COMPLEXES THEREOF AND USES THEREOF IN ASYMMETRIC REACTIONS

... ²²²Chiral ligands and transition metal complexes based on such chiral ligands ²useful in asymmetric catalysis are disclosed. The chiral ligands include ²phospholanes, P, N ligands, N, N ligands, biphenols, and chelating phosphines. ²The ferrocene-based irridium (R,R)-f-binaphane complex reduces imines to the ²corresponding amines with 95-99.6 % enantioselectivity and reduces .beta.-²substituted-.alpha.-arylenamides with 95 % enantioselectivity. The transition ²metal complexes of the chiral ligands are useful in asymmetric reactions such ²as asymmetric hydrogenation of imines, asymmetric hydride transfer reactions, ²hydrosilylation, hydroboration, hydrovinylation, hydroformylation, allylic ²alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, ²isomerization, Aldol reaction, Michael addition and epoxidation reactions.² ...

METHOD OF PRODUCING OPTICALLY ACTIVE N-(HALOPROPYL)AMINO ACID DERIVATIVE

It is intended to provide a process for producing an optically active N-(halopropyl)amino acid derivative. This method comprises: the step wherein an optically active alanine ester represented by the formula (I) or its salt (hereinafter sometimes referred to simply as alanine ester) is reacted with a halogenated propane represented by the formula (II) to give a compound represented by the formula (III):and the step wherein a protective group is introduced into the nitrogen atom in the compound represented by the formula (III) as described above to thereby give an optically active N-(halopropyl)amino acid derivative represented by the formula (IV). It is intended to provide a method of effectively producing an optically active N-(halopropyl)amino acid derivative.

ORTHO SUBSTITUTED CHIRAL PHOSPHINES AND PHOSPHINITES AND THEIR USE IN ASYMMETRIC CATALYTIC REACTIONS

... 3,3'-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. Provided, for example, are ligands of the formula: (see above formula) The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition. epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta- hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.

OPTICAL RESOLUTION OF 1-T-BUTYLAMINO-2,3-DIHYDROXYPROPANE

Process for resolving enantiomers of 1-t-butyl-amino-2,3-dihydroxypropane using a pyroglutamic acid or a tartaric acid as resolving agent. The enantiomers of 1-t-butylamino-2,3-dihydroxypropane are useful in preparing .beta.-adrenergic blocking agents.

DIPHOSPHINES, PREPARATION AND USES THEREOF

La présente invention a pour objet de nouvelles diphosphines de Formule (I) notamment utiles, sous leur forme optiquement active, à titre de ligands dans des complexes métalliques. La présente invention concerne également leurs utilisations comme produits intermédiaires dans la préparation de ligands sous une forme insoluble de type polymérique. L'invention vise également l'utilisation desdits ligands insolubles notamment dans la préparation de complexes métalliques destinés à la catalyse asymétrique.

PRODUCTION OF OPTICALLY ACTIVE PHOSPHOLANES

The invention relates to phospholanes and diphospholanes of general formula (I), whereby R represents H, C1-C6-alkyl, aryl, alkyl aryl, SiR23, R2 represents alkyl or aryl, A represents H, C1-C6-alkyl, aryl, Cl, or (a), and B represents a binding link with 1-5 C-atoms between both P-atoms. The invention also relates to the use of said phospholanes and diphospholanes as a catalyst in asymmetric synthesis.

METHOD FOR THE PRODUCTION OF PRAZIQUANTEL AND PRECURSORS THEREOF

The present invention provides methods of preparing Praziquantel, in particular (R)-Praziquantel and analogues thereof in a stereoselective manner. One method involves asymmetric hydrogenation of the following intermediate compound (I) and subsequent cyclization.

PROCESSES FOR THE PREPARATION OF DASOTRALINE AND INTERMEDIATES THEREOF

The present invention provides processes for the preparation of Dasotraline (1), as well as intermediates useful in the preparation thereof. In particular, processes are provided for the production of the compound of Formula (2), or a salt thereof, and its deprotection to afford Dasotraline (1). (See Formula 2) ...

MIXTURES OF CHIRAL MONOPHOSPHORUS COMPOUNDS USED AS LIGAND SYSTEMS FOR ASYMMETRIC TRANSITION METAL CATALYSIS

The invention relates to certain chiral transition metal catalysts, to the metal of which at least two structurally different monophosphorus ligands are bonded, at least one of said monophosphorus ligands being chiral. Said chiral transition metal catalysts are suitable as catalysts for use in asymmetric transition metal-catalyzed reactions, providing better enantioselectivities than in cases where only one structurally defined ligand is used.

PROCESS FOR PRODUCTION OF ETHYLENEDIAMINE DERIVATIVES HAVINGHALOGENATED CARBAMATE GROUP AND ACYL GROUP, AND INTERMEDIATED FOR PRODUCTION OF THEDERIVATIVES

An ethylenediamine derivative having a halogenated carbamate group and an acyl group can be produced by performing the catalytic hydrogenation of an aminonitrile having a halogen-substituted carbamate group in the presence of an acid and then performing the acylation of the resulting product. The aminonitrile (i.e., a starting material) can be prepared in a high yield by performing the halogenated carbamatation of an amino acid amide in the presence of water and then reacting the resulting product with a deoxidizing agent such as vilsmeier reagent.

A METHOD FOR MANUFACTURING A ß-DIARYL ELECTRON WITHDRAWING GROUP SUBSTITUTED COMPOUND

Disclosed is a method for producing a .beta.-diaryl electron-withdrawing group substituted compound at high yield with high selectivity. Specifically , an optically active .beta.-diaryl electron-withdrawing group substituted c ompound represented by the general formula (V) below is produced by reacting an electron-withdrawing group substituted-.beta.-arylolefin derivative repr esented by the general formula (I) below with an arylboron represented by th e following general formula (II): Ar2-BXmMn in the presence of a compound re presented by the following general formula (IV): RhYoL1 p(Chiraphos)q (where in Y represents ClO4, BF4, PF6, SbF6, OTf, a halogen atom, a hydroxy group, an alkoxy group or an acyloxy group, and L1 represents an organic ligand). [ chemical formula 1] (I) (In the formula, Ar1 represents an aryl group, and E represents a formyl group, an acyl group or the like.) [chemical formula 3] (V) ...

ASYMMETRIC REDUCTION METHOD

A PROCESS AND AN APPARATUS FOR PRODUCING EPISESAMIN-RICH COMPOSITIONS

To provide a process and an apparatus by means of which a composition that contains episesamin in a concentration greater than 50 wt% on the basis of the sum weight of sesamin and episesamin can be produced conveniently and at high yield. There are provided a process and an apparatus which comprise the step of applying epimerization to sesamin or a sesamin-containing composition so that at least part of the sesamin is converted to episesamin and the step of selectively crystallizing episesamin by recrystallization and by means of which a composition that contains episesamin in a concentration greater than 50 wt% can be produced conveniently and at high yield.

METHOD FOR PRODUCING SPIROOXINDOLE DERIVATIVE

The present invention is intended to provide a method for efficiently producing and providing a compound having a spirooxindole skeleton, for example, a compound having a spirooxindole skeleton and having antitumor activity that inhibits the interaction between Mdm2 protein and p53 protein, or an intermediate thereof, using an asymmetric catalyst. A compound having an optically active tricyclic dispiroindole skeleton is efficiently obtained through a catalytic asymmetric 1,3-dipolar cycloaddition reaction using ketimine as a reaction substrate and using a chiral ligand and a Lewis acid.

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE EPOXY COMPOUND

... [PROBLEMS] To provide a process for producing an optically active epoxy c ompound. [MEANS FOR SOLVING PROBLEMS] Disclosed is an industrially useful pr ocess for producing an optically active epoxy compound. In the reaction betw een an unsaturated compound and an oxidizing agent in the presence of an opt ically active titanium-salen complex, an optically active titanium-salalen c omplex or an optically active titanium-salan complex, it is found that the a ddition of a buffering agent or a buffer solution to the reaction system ena bles to reduce the decomposition of the catalyst, reduce the amount of the c atalyst used, and reduce the production of a by-product compared to a conven tional process, and can produce a high-quality, optically active epoxy compo und in high chemical yield and with high optical purity.

MODULATORS OF THE PROSTACYCLIN (PGI2) RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO

The present invention relates to amide derivatives of Formula (XIIIa) and pharmaceutical compositions thereof that modulate the activity of the PGI2 receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of: pulmonary arterial hypertension (PAH); idiopathic PAH; familial PAH; PAH associated with a collagen vascular disease, a congenital heart disease, portal hypertension, HIV infection, ingestion of a drug or toxin, hereditary hemorrhagic telangiectasia, splenectomy, pulmonary veno-occlusive disease (PVOD) or pulmonary capillary hemangiomatosis (PCH); PAH with significant venous or capillary involvement; platelet aggregation; coronary artery disease; myocardial infarction; transient ischemic attack; angina; stroke; ischemia-reperfusion injury; restenosis; atrial fibrillation; blood clot formation in an angioplasty or coronary bypass surgery individual or in an individual suffering from atrial fibrillation; atherosclerosis ...

Novel method for producing optically active pyrrolidine compound

[Object] A novel method for producing an optically active pyrrolidine compound, which is useful as a production intermediate of a pharmaceutical, and a production intermediate thereof, is provided. [Means for Solution] According to the production method of the present invention, a chloro compound that is a key intermediate can be produced efficiently industrially by subjecting a mixture of regioisomers obtained by reacting an optically active epoxy compound substituted with aryl, which is easily available, with an amine compound, to chlorination. Furthermore, an optically active pyrrolidine compound can be produced industrially efficiently with the key intermediate. [Selected Figure] None

Process for Production of Camptothecin Derivative

Disclosed is a process for production of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]-carbonyloxycamptothecin from a camptothecin composition containing 18,19-dehydrocamptothecin without producing any vinyl form of the compound. The process is characterized by catalytically reducing at least one compound selected from a compound (1) and others in the process of producing a compound (5) from a composition containing the compound (1).

Ruthenium (ii) catalysts for use in stereoselective cyclopropanations

Chiral ruthenium catalysts comprising salen and alkenyl ligands are provided for stereoselective cyclopropanation, and methods of cyclopropanation are provided. The chiral ruthenium catalyst is prepared in situ by combining an alkenyl ligand, a deprotonated chiral salen ligand, and a ruthenium (II) metal. A preferred catalyst is prepared in situ by combining 2,3-dihydro-4-venylbenzofuran, deprotonated 1,2-cyclohexanediamino-N,N′-bis(3,5-di-t-butyl-salicylidene) and RuCl 2 (p-cymene)] 2 .

Process for producing (3s)-i-menthyl 3-hydroxybutyrate and sensate composition

Disclosed is a cooling component or sensate component which does not have undesirable stimulus feeling, bitterness and the like and is excellent in the persistence of refresh-feeling and cool-feeling, a sensate composition which comprises the same, and various products that comprise said sensate composition. Also disclosed is a cooling agent comprising (3S)-l-menthyl 3-hydroxybutyrate represented by the following formula (I)

Bis-phosphate compound and asymmetric reaction using the same

A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-phosphate compound has a tetraaryl skeleton represented by General Formula (1). In an asymmetric reaction, an amidodiene and an unsaturated aldehyde compound are reacted with each other in the presence of the optically active bis-phosphate compound to give an optically active amidoaldehyde. The invention allows a reaction such as an asymmetric Diels-Alder reaction to proceed efficiently, which has been difficult with conventional mono-phosphate compounds. Thus, the invention enables an industrially feasible method for the production of optically active amidoaldehydes, optically active β-amino acid derivatives, optically active diamine compounds, optically active pyrrolidine derivatives and optically active dihydropyran derivatives which are useful as products such as medicines, agricultural chemicals and chemical products as well as synthesis intermediates for such products.

Method for preparing optically active 1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane

A method for preparing optically active 1-bromo-1-[3,5-bis(trifluoromethyl)-phenyl]ethane having a high optical purity, which comprises the step of brominating optically active 1-[3,5-bis(trifluoromethyl)phenyl]ethanol by using, as a brominating agent, (a) a combination of a phosphorus halide and hydrogen bromide, (b) a combination of 1,2-dibromo-1,1,2,2-tetrachloroethane and an organic phosphorous compound represented by the general formula (I): P(R 1 )(R 2 )(R 3 ) (in the formula, R 1 , R 2 , and R 3 independently represent a C 6-10 aryl group, a C 6-10 aryloxy group, a C 1-10 alkyl group, a C 1-10 alkoxyl group, a C 3-6 cycloalkyl group, or a C 3-6 cycloalkoxy group), or (c) a combination of N-bromosuccinimide and a dialkyl sulfide.

Compound having hetero ring skeleton, and process for producing optically active compound using the aforementioned compound as asymmetric catalyst

The invention provides a compound having a heterocyclic skeleton of formula (I): wherein the substituents are as defined in the specification, as well as a tautomer thereof or a salt thereof. The invention also provides asymmetric synthesis methods involving the use of such a compound, tautomer thereof, or salt thereof, as a catalyst.

Chiral 1-(4-methylphenylmethyl)-5-oxo--pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion

Chiral 1-(4-methylphenylmethyl)-5-oxo-{N-[(3-t-butoxycarbonyl-aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion The present invention provides chiral (2S)-1-(4-methyl-phenylmethyl)-5-oxo-(3S)-{N-[(3-t butoxycarbonyl aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamide, and (2S)-1-(4-methylphenylmethyl)-5-oxo-(3R)-{N-[(3-t-butoxycarbonyl amino methyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamide of formula 6 and 7 respectively. The present invention also relates to use of these moieties as inhibitors of collagen induced platelet adhesion and aggregation mediated through collagen receptors. The present invention provides a process for preparation of chiral carboxamides of formula 6 and 7 using the process which has advantage to avoid any racemization at the a-carboxylic center, during N-alkylation. The reagent LiHMDS is used at low temperatures to furnish methyl N-(p methylphenylmethyl)lpyroglutamate in good chiral purity.

METHOD FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID ESTER

Provided is a method for producing an optically active carboxylic acid ester at a high yield and with high enantioselectivity using dynamic kinetic resolution, said optically active carboxylic acid ester having an α-nitrogen substituent. This method for producing an optically active carboxylic acid ester includes a step in which racemic carboxylic acid represented by formula (a) and a specific alcohol or phenol derivative are reacted in a polar solvent having a dipole moment of at least 3.5 in the presence of an acid anhydride and an asymmetric catalyst, one enantiomer of the racemic carboxylic acid is selectively esterified, and the other enantiomer is racemized. In formula (a), Ra1 represents a nitrogen-containing heteroaromatic ring group bonded to an assymetric carbon via a nitrogen atom constituting a ring, and Ra2 is an organic group. 3. The method for producing an optically active carboxylic acid ester according to claim 1 , wherein Rin formula (a) is a 1H-pyrrol-1-yl group.4. The method for producing an optically active carboxylic acid ester according to claim 1 , wherein the polar solvent having a dipole moment of 3.5 or more is dimethylacetamide claim 1 , dimethylformamide claim 1 , 1 claim 1 ,3-dimethyl-2-imidazolidinone claim 1 , N-methylpyrrolidone claim 1 , or dimethyl sulfoxide.5. The method for producing an optically active carboxylic acid ester according to claim 1 , wherein the step is performed in the presence of a base.7. The method for producing an optically active carboxylic acid ester according to claim 6 , wherein at least one of R claim 6 , R claim 6 , or Ris a methyl group.8. The method for producing an optically active carboxylic acid ester according to claim 6 , wherein the base is diisopropylethylamine claim 6 , triethylamine claim 6 , dimethylethylamine claim 6 , dimethylisopropylamine claim 6 , diethylmethylamine claim 6 , or diisopropylmethylamine.10. The method for producing an optically active carboxylic acid ester according to ...

Metallorganocatalysis For Asymmetric Transformations

A ligand having the structure or its enantiomer; (I) wherein: each one of R a , R b , R c and R d is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH 2 NH; *CH(CH 3 )NH(C*,R); and the organocatalyst is an organic molecule catalyst covalently bound to the bridge group. Also, a catalyst having the structure or its enantiomer: (II) wherein: each one of R a , R b , R c and R d is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH 2 NH; *CH(CH 3 )NH(C*,R); and *CH(CH 3 )NH(C*,S); the organocatalyst is an organic molecule catalyst covalently bound to the bridge group; and M is selected from the group consisting of Rh, Pd, Cu, Ru, Ir, Ag, Au, Zn, Ni, Co, and Fe.

Method for manufacturing optically active compound

The present invention provides a method for manufacturing an optically active compound of formula (2), which contains bringing hydrogen into contact with a compound of formula (1) in the presence of a transition metal catalyst having an optically active ligand. In the formula, R 1 represents a hydrogen atom or an acetyl group, R 2 , R 3 , R 4 , and R 5 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group, an amino group, or an acyl group, R 6 represents an alkyl group, R 7 and R 8 each independently represents a hydrogen atom or an alkyl group, and a carbon atom marked with an asterisk (*) represents an asymmetric carbon atom.

METHOD FOR PRODUCING OPTICALLY ACTIVE PYRROLIDINE COMPOUNDS

The present invention provides a process for preparing a compound represented by formula (VII), which comprises reacting a compound represented by formula (VI) with a malonic acid derivative in the presence of a base and an asymmetric catalyst in a two layer solvent system of hydrophobic solvent and water. 3. The process according to claim 2 , which comprises conducting a step for preparing the compound represented by formula (VI) from the compound represented by formula (V) in a hydrophobic solvent claim 2 , wherein the hydrophobic solvent is the same hydrophobic solvent that is used in the step for preparing the compound represented by formula (VII) from the compound represented by formula (VI).5. The process according to claim 4 , which comprises conducting the step for preparing the compound represented by formula (V) from the compound represented by formula (III) and the step for preparing the compound represented by formula (VI) from the compound represented by formula (V) in a hydrophobic solvent claim 4 , wherein the hydrophobic solvent is the same solvent that is used in the step for preparing the compound represented by formula (VII) from the compound represented by formula (VI).6. The process according to claim 4 , which comprises conducting a step for preparing the compound represented by formula (V) from the compound represented by formula (III) in a two layer solvent system of the hydrophobic solvent and water claim 4 , and comprises conducting a step for preparing the compound represented by formula (VI) from the compound represented by formula (V) in a hydrophobic solvent claim 4 , wherein the hydrophobic solvent that is used in these steps is the same hydrophobic solvent that is used in a step for preparing a compound represented by formula (VII) from a compound represented by formula (VI).8. The process according to claim 7 , which comprises applying as a starting material the compound represented by formula (VII) without isolating it to the ...

Chelate-controlled diastereoselective hydrogenation with heterogeneous catalyst

A catalyst, method of using, and use of a hydrogenation catalyst, preferably palladium on a support, preferably alumina or activated charcoal support. This in the presence of lithium salts, with salts such as the borates being preferred. This provides hydrogenation of precursors to give rise to a stereoselective, such as diastereoselective bias in the product of alkene hydrogenation using the catalyst. This equation, using the preferred substrate, best illustrates the invention:

SYNTHESIS PROCESS FOR CHIRAL CYCLOPROPYL ETHYNYL TERTIARY ALCOHOL COMPOUND

Provided is a synthesis process for a chiral cyclopropyl ethynyl tertiary alcohol compound, where a chiral amino alcohol or a chiral amino diol is reacted in the presence of an alkaline reagent and a salt to obtain an optically active propynyl alcohol compound. In particular, the process includes (1) reacting cyclopropyl acetylene with a chiral inducing agent, a chiral auxiliary reagent and zinc halide in an organic solvent in the presence of an alkaline reagent and a sulfonate or a sulphinate to obtain a first reaction mixture; (2) reacting the resultant first reaction mixture with 5-chloro-2-aminotrifluorobenzophenone to form (S)-2-amino-5-chloro-α-cyclopropyl acetylene-α-trifluoromethylbenzyl alcohol. The process avoids an organic zinc reagent and a Grignard reagent, and has the advantages of safe production, an environmentally friendly route, low production costs, a high resultant product yield, a high chiral ee value and is suitable for industrial production. 2. The method according to claim 1 , wherein said salt is a sulfonate.3. The method according to claim 1 , wherein the organic solvent is selected from the group consisting of: tetrahydrofuran claim 1 , toluene claim 1 , methyl tert-butyl ether claim 1 , N-methylpyrrolidone claim 1 , dioxane claim 1 , diethyl ether claim 1 , substituted or unsubstituted alkylbenzene claim 1 , benzene claim 1 , dichloromethane claim 1 , cyclohexane claim 1 , n-hexane claim 1 , or combinations thereof.4. The method according to claim 1 , wherein the alkaline agent is selected from alkali hydrides claim 1 , sodium alkoxides claim 1 , potassium alkoxides claim 1 , or combinations thereof; preferably NaH.5. The method according to claim 1 , characterized in that the sulfonate is selected from alkyl sulfonates claim 1 , substituted or unsubstituted aryl sulfonates claim 1 , or combinations thereof; and/orThe sulfinate is selected from alkyl sulfinate, substituted or unsubstituted aryl sulfinate, or combinations thereof.6. The ...

Method for producing optically active valeric acid derivative

A method for producing a compound (4), which comprises allowing a compound (1) to react with hydrogen gas in an inert solvent, in the presence of a specific chiral ligand and a ruthenium catalyst, or in the presence of an asymmetric transition metal complex catalyst previously generated from the chiral ligand and the ruthenium catalyst.

Rhodium catalyst and method for producing amine compound

[Problem] Provision of a superior rhodium catalyst and a production method of amine compound. [Solving Means] A rhodium complex coordinated with a compound represented by the formula

A METHOD FOR DIRECTLY CONSTRUCTING HIGHLY OPTICALLY ACTIVE TETRASUBSTITUTED ALLENIC ACID COMPOUNDS

The present invention discloses a method for directly constructing highly optically active tetrasubstituted allenic acid compounds, i.e., a one-step process for directly constructing highly optically active axially chiral tetrasubstituted allenic acid compounds by using tertiary propargyl alcohol, carbon monoxide and water as reactants in an organic solvent in the presence of palladium catalyst, chiral diphosphine ligand, monophosphine ligand and organic phosphoric acid. The method of the present invention has the following advantages: operations are simple, raw materials and reagents are readily available, the reaction conditions are mild, the substrate has high universality, the functional group has good compatibility, and the reaction has high enantioselectivity (90%˜>99% ee). The highly optically active allenic acid compounds obtained by the present invention can be used as an important intermediate to construct γ-butyrolactone compounds containing tetrasubstituted chiral quaternary carbon centers, tetrasubstituted allenic alcohol and other compounds. 2. The method of claim 1 , wherein claim 1 , Ris a C1-C20 alkyl claim 1 , a C1-C20 alkyl with functional group at the end claim 1 , phenyl claim 1 , aryl or heterocyclic group; Ris a C1-C10 alkyl claim 1 , a C1-C10 alkyl with functional group at the end claim 1 , phenyl claim 1 , aryl or heterocyclic group; Ris a C1-C10 alkyl claim 1 , a C1-C10 alkyl with functional group at the end claim 1 , phenyl claim 1 , aryl or heterocyclic group; wherein claim 1 , the functional group of the C1-C20 alkyl or C1-C10 alkyl with functional group at the end claim 1 , is selected from carbon-carbon double bond claim 1 , carbon-carbon triple bond claim 1 , ester group claim 1 , hydroxyl group claim 1 , acyl group claim 1 , acyloxy group claim 1 , amide group claim 1 , halogen claim 1 , carboxyl group claim 1 , cyano group; the said aryl is a phenyl with electron-withdrawing or electron-donating substituents at the ortho claim 1 , ...

Process for making novel chiral phosphorus ligands

Disclosed are methods for making chiral phosphorus ligands including chiral phosphines, chiral phosphine oxides, phosphonamides, and aminophosphines. The chiral phosphorus ligands prepared by the methods of the invention are useful as components of chiral catalysts, e.g., transition metal complexes.

1-amino-2-vinylcyclopropane carboxylic acid amide and salt thereof, and method for producing same

The present invention relates to 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof. By obtaining optically active 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof by hydrolyzing optically active 1-amino-2-vinylcyclopropane carbonitrile or a salt thereof according to the production method of the present invention, 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof, which is useful as a pharmaceutical/agrochemical intermediate, can be easily obtained. The present invention is capable of providing a substrate to be subjected to optical resolution, which enables the production of optically active 1-amino-2-vinylcyclopropane carboxylic acid, which is widely used as a raw material for pharmaceutical and agrochemical products and is especially important as an intermediate for therapeutic agents for hepatitis C, inexpensively with high purity and high yield.

ENANTIOPURE TERPHENYLS WITH TWO ORTHO-ATROPISOMERIC AXES

Enantiopure terphenyl presenting two ortho-located chiral axes having the following structural formula (I): their process of synthesis and their use as mono or bidentate ligands for asymmetric organometallic reactions, as organocatalysts, as chiral base and as generator, with metal, of isolable chiral metallic complexes for applications in asymmetric catalysis and others. 2. The enantiopure terphenyl according to claim 1 , wherein{'sub': '1', 'claim-text': an halogen atom,', 'a substituted or unsubstituted branched or straight alkyl group or', 'a substituted or unsubstituted branched or straight alkoxy group or', {'sub': '3', 'a CFgroup,'}], 'Rrepresents'}{'sub': '2', 'claim-text': a hydrogen atom or', 'a substituted or unsubstituted branched or straight alkyl group, or', 'a substituted or unsubstituted branched or straight alkoxy group, 'Rrepresents'}{'sub': '3', 'claim-text': a substituted or unsubstituted branched or straight alkyl group or', 'a substituted or unsubstituted branched or straight alkoxy group,, 'Rrepresents'}{'sub': '4', 'claim-text': a hydrogen atom or', 'a halogen atom or', 'a substituted or unsubstituted branched or straight alkoxy group, or', 'a substituted or unsubstituted branched or straight alkyl group or', 'a aryl group or', {'sub': 2', '2', 'n+2, 'a CHF group, or a CHFgroup or —CnFgroup avec n=1 à 10, or'}], 'Rrepresents'}{'sub': '5', 'claim-text': [{'sub': a', 'a', '1', '4, 'a SORgroup with Rselected from a substituted or unsubstituted branched or straight-(C-C) alkyl group or a substituted or unsubstituted aryl group, or'}, 'a OH group, or', {'sub': a', 'd', 'a', 'd', 'a', 'd, '—PRnor a —P(O)Rnwith Rand Rindependently selected from a substituted or unsubstituted branched or straight alkyl group or a substituted or unsubstituted aryl group,'}], 'Rrepresents'}{'sub': '6', 'claim-text': a hydrogen atom,', 'a halogen atom or', {'sub': 1', '4, 'a substituted or unsubstituted branched or straight-(C-C) alkyl group or'}, {'sub': 1', '4, 'a ...

Novel Chiral Alfa-Amino Tertiary Boronic Esters

The present disclosure relates to a novel, highly efficient and enantiospecific borylation method to synthesize a wide range of enantiopure alfa-amino tertiary boronic esters, and novel alfa-amino tertiary boronic acids and esters prepared by the method. More specifically, highly enantiospecific borylation of configurationally stable α-N-Boc substituted tertiary organolithium species and HBpin has been developed to synthesize various alfa-amino tertiary boronic esters through the formation of a new C—B bond with excellent enantiopurities. 2. The method of claim 1 , wherein R claim 1 , Rand Rare each individually different straight or branched optionally substituted C-Calkyl group claim 1 , optionally substituted C-Ccycloalkyl group claim 1 , optionally substituted C-Ccycloalkenyl group claim 1 , straight or branched optionally substituted C-Calkenyl group claim 1 , straight or branched optionally substituted C-Calkynyl group claim 1 , optionally substituted C-Caryl claim 1 , optionally substituted C-Cheteroaryl with one or more O claim 1 , N claim 1 , or S claim 1 , wherein Rand R claim 1 , Rand R claim 1 , or Rand Rmay jointly form an optionally substituted C-Csaturated or non-saturated ring claim 1 , or form an optionally substituted C-Csaturated or non-saturated heterocyclic ring.3. The method of claim 1 , wherein B(OR)(OR)Ris B(OMe) claim 1 , catecholborane claim 1 , or 4 claim 1 ,4 claim 1 ,5 claim 1 ,5-tetramethyl-1 claim 1 ,3 claim 1 ,2-dioxaborolane (HBpin) claim 1 , 2-methoxy-4 claim 1 ,4 claim 1 ,5 claim 1 ,5-tetramethyl-1 claim 1 ,3 claim 1 ,2-dioxaborolane (MeO-Bpin).4. The method of claim 1 , wherein the NPG is a nitrogen protecting group that has a carbonyl (C═O) group claim 1 , a sulfinyl group ((S═O) claim 1 , or a sulfonyl (—SO)— group directly attached to the nitrogen to be protected.5. The method of claim 1 , wherein the NPG is tert-butyloxycarbonyl (Boc) or CON(Pr).6. The method of claim 1 , wherein LiRis lithium diisopropylamide (LDA) claim 1 , ...

PROCESS FOR PREPARING SPIROCYCLIC COMPOUNDS

New spirocyclic ligands for use in metal catalysed asymmetric hydrogenation, hydroformylation, allylic substitution and a process for the production of the same from plant feedstocks. 1. A process for the production of of spirocyclic compounds , said process including the steps of;introducing or mixing at least one halogenated heterocyclic compound with iron or an iron containing complex; andintroducing at least one organometallic compound.2. A process according to wherein the iron containing complex includes iron (III).3. A process according to wherein the iron or iron containing complex is in a catalytic amount.4. A process according to wherein the process includes substantially 5 mol. % of iron (III) catalyst.5. A process according to wherein the process ues any one or any combination of Fe(acac)3 claim 4 , FeCl3 claim 4 , Fe(dbm)3 and/or the like.6. A process according to wherein the organometallic compound is an aryl and/or alkyl magnesium halide (Grignard reagent).7. A process according to wherein the organometallic compound is an organozinc reagent.8. A process according to wherein the halogenated heterocycle is derived from plants or plant related compounds.9. Iron(III)-catalyzed arylative spirocyclization of at least one halogenated heterocyclic compound.11. A ligand according to wherein Ar is an aromatic group.12. A ligand according to wherein L is a Lewis base ligating group. The present invention relates to the catalytic production of spirocyclic compounds and processes including said catalysts.Although the following description refers exclusively to the production of spirocyclic compounds the skilled person will appreciate that the present method is not limited to the production of such compounds and other heterocyclic compounds can be produced. In addition, plant derived precursors are utilised, however the person skilled in the art will appreciate that other conventional precursors could be used and the invention is not limited to as such.Methods to ...

Method for producing optically active substance, optically active substance, method for producing chiral molecule, and chiral molecule

Provided is a method for producing an optically active substance, the method including an asymmetric induction, wherein an asymmetry inducer is allowed to act on a chiral molecule having a half-life of enantiomeric excess of shorter than 10 hours, thereby increasing abundance of one enantiomer of the chiral molecule. According to this method, one enantiomer of a chiral molecule that is susceptible to racemization can be selectively and efficiently obtained.

Highly z-selective and enantioselective ring opening/cross metathesis catalyzed by a resolved stereogenic-at-ru complex

This invention relates generally to enantiomerically enriched C—H activated ruthenium olefin metathesis catalyst compounds which are stereogenic at ruthenium, to the preparation of such compounds, and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in enantio- and Z-selective olefin metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

PROCESS FOR MANUFACTURE AND RESOLUTION OF 2-ACYLAMINO-3-DIPHENYLPROPANOIC ACID

The invention relates to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, in particular neutral endopeptidase (NEP) inhibitors. 2. The process according to claim 1 , whereinR1 is methyl, ethyl, phenyl or para-chlorophenyl,R2 is methyl, andR6 is phenyl.3. The process according to claim 2 , wherein the decarboxylation reaction conditions are achieved by heating at a temperature of from 80 deg C. to 250 deg C.4. The process according to claim 1 , wherein in step (i) the decarboxylation reaction is carried out without a solvent claim 1 , or in a solvent selected from water claim 1 , toluene claim 1 , xylene claim 1 , ethylbenzene claim 1 , chlorobenzene claim 1 , dichlorobenzene claim 1 , nitrobenzene claim 1 , N claim 1 ,N-dimethyl formamide (DMF) and 1-methyl-2-pyrrolidone (NMP) and at the reflux temperature of said solvent.8. The process according to claim 1 , wherein in step (iii) the acidic reagent is an inorganic acid or an organic acid selected from hydrochloric acid claim 1 , sulfuric acid claim 1 , phosphoric acid claim 1 , oxalic acid claim 1 , citric acid claim 1 , formic acid and acetic acid.10. The process according to claim 9 , whereinR1 is methyl, ethyl, phenyl or para-chlorophenyl,R2 is methyl, andR6 is phenyl.14. The process according to claim 9 , wherein in step (ii) the acidic reagent is an inorganic acid or an organic acid selected from hydrochloric acid claim 9 , sulfuric acid claim 9 , phosphoric acid claim 9 , oxalic acid claim 9 , citric acid claim 9 , formic acid and acetic acid.16. The process according to claim 15 , whereinR1 is methyl, ethyl, phenyl or para-chlorophenyl,R2 is methyl, andR6 is phenyl.17. The process according to claim 15 , wherein the acidic reagent is an inorganic acid or an organic acid selected from hydrochloric acid claim 15 , sulfuric acid claim 15 , phosphoric acid claim 15 , oxalic acid claim 15 , citric acid claim 15 , formic acid or acetic acid. ...

A METHOD FOR PREPARING OPTICALLY ACTIVE CARBONYL COMPOUND

The present invention discloses a method for preparing optically active carbonyl compound, comprising the following steps: under the catalysis of chiral amine salt and transition metal catalysts, with hydrogen and catalytic amount of dihydropyridine compound as hydrogen source, use α, β-unsaturated aldehydes or α, β-unsaturated troponoid compounds to conduct asymmetric catalytic reaction to obtain the optically active carbonyl compound. This method comes in moderate reaction condition, simple operation, and catalytic amount of dihydropyridine compounds usage, the target product is easy to be separated and purified from the reaction system, and the metal catalyst can be recycled, it is economical. 2. The method for preparing an optically active carbonyl compound according to claim 1 , which is characterized in that: in the R claim 1 , Rand R claim 1 , alkyl is alkyl containing 1 to 30 carbon atoms;heteroaryl is aromatic heterocyclic aryls containing 3 to 9 carbon atoms;alkoxy is cyclo-alkoxy or linear or branched alkoxys containing 1 to 30 carbon atoms, and these alkoxys can be substituted by fluorine, chlorine, bromine, iodine, hydroxy or aryl;acylaminos are acylaminos containing 1 to 20 carbon atoms.3. The method for preparing an optically active carbonyl compound according to claim 2 , which is characterized in that: the heteroaryl is: 2-furyl claim 2 , 2-pyrryl claim 2 , 2-thienyl claim 2 , 2-pyridyl claim 2 , 2-indolyl claim 2 , 3-furyl claim 2 , 3-pyrryl claim 2 , 3-thienyl claim 2 , 3-pyridyl claim 2 , or 3-indolyl;the alkoxies are: methoxyl, ethyoxyl, n-propoxyethyl, isopropoxy, n-butoxy, isobutoxy, 2-butoxy, tert-butoxy, n-pentyloxy, 2-pentyloxy, 2-pentyloxy, tert-pentyloxy, n-hexyloxy, cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, phenylmethoxy, 1-phenylethoxy, or 2- ...

ION PAIR CATALYSIS OF TUNGSTATE AND MOLYBDATE

The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides. 2. The complex of claim 1 , wherein:{'sub': 1', '1-3', '3, 'each Rindependently represents Calkyl-phenyl, which phenyl group is substituted by from two to four Rsubstituents;'}{'sub': 2', '4, 'each Rindependently represents phenyl, which group is unsubstituted or substituted by from one to two Rsubstituents;'}{'sub': 3', '4', '1-6', '3-6', '5, 'each Rand Rindependently represents fluoro, branched or unbranched Calkyl, Ccycloalkyl, which latter two groups are unsubstituted or substituted by one or more halogen atoms) or OR;'}{'sub': 1-3', '3-6, 'R5 represents branched or unbranched Calkyl or Ccycloalkyl, which groups are unsubstituted or substituted by one or more halogen atoms.'}3. (canceled)4. The complex of claim 1 , wherein the organic cation (A) is enantioenriched.5. The complex of claim 1 , where the organic cation (A) is selected from:(i) 1,4-bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium;(ii) 1,4-bis((4R,5R)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium;(iii) 1,4-bis((4S,5S)-1,3-bis(3,5-di-tert-butyl-4-methoxybenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium;(iv) 1,4-bis((4R,5R)-1,3-bis(3,5-di-tert-butyl-4-methoxybenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium;(v) 1,4-bis((4S,5S)-1,3-bis(3,5-di-tert-butyl-4-fluorobenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium; and(vi) 1,4-bis((4R,5R)-1,3-bis(3,5-di-tert-butyl-4-fluorobenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium.6. The complex of claim 5 , where the organic ...

PROCESS FOR THE SYNTHESIS OF NON-RACEMIC CYCLOHEXENES

This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R, R, R, R, R, R, R, R, Rand Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R, R, R, R, R, R, R, R, Z and Z′ have the meanings as defined in the description. 2. The process according to wherein claim 1 , in the formulae (I) and (II) claim 1 , Ris C-C-alkyl and Rand Rare both hydrogen.3. The process according to wherein claim 1 , in the formulae (I) and (II) claim 1 , Ris methyl and Rand Rare both hydrogen.4. The process according to wherein claim 1 , in the formulae (I) and (III) claim 1 , Ris C-C-alkyl and R claim 1 , R claim 1 , R claim 1 , Rand Rare each hydrogen.5. The process according to wherein claim 1 , in the formulae (I) and (III) claim 1 , Ris methyl and R claim 1 , R claim 1 , R claim 1 , Rand Rare each hydrogen.6. The process according to wherein claim 1 , in the formulae (I) and (II) claim 1 , Y is OC(O)Rwherein Ris selected from C-C-aryl and di(C-C-aryl)-C-C-alkyl.7. The process according to wherein claim 1 , in the formulae (I) and (II) claim 1 , Y is OC(O)Rwherein Ris selected from phenyl and diphenylmethyl.8. The process according to wherein the metal M is selected from Scandium (Sc) claim 1 , Yttrium (Y) claim 1 , Terbium (Tb) and Ytterbium (Yb).9. The process according to wherein the metal M is Yttrium (Y) or Ytterbium (Yb).10. The process according to wherein the ...

PRODUCTION METHOD FOR OPTICALLY ACTIVE ALCOHOL COMPOUND

A method for stereoselectively producing an optically active alcohol compound. The optically active alcohol compound of Formula (8) can be produced in high yield and high selectivity from the compound of Formula (3), and the production method that is useful industrially and the intermediates therefor can be provided. In formulae, Ris a hydrogen atom, Calkyl, Calkyl optionally substituted with R, or the like, Ris cyano or —CHN(R)R, and Ris Ccycloalkyl. 2. The method for producing the optically active alcohol compound according to claim 1 , wherein Ris a hydrogen atom claim 1 , (C) alkyl optionally substituted with R claim 1 , —C(O)R— claim 1 , or —Si(R)(R)R.3. The method for producing the optically active alcohol compound according to claim 2 , wherein the reaction is carried out in the presence of the optically active ruthenium catalyst of Formula (4).4. The method for producing the optically active alcohol compound according to claim 3 , wherein{'sup': 2', '5', '4, 'sub': '2', 'Ris —CHN(R)R;'}{'sup': 4', '6', '7, 'Ris —C(O)Ror —C(O)OR;'}{'sup': '6', 'sub': 1-6', '1-6, 'Ris Calkyl or (C) alkyl optionally substituted with a halogen atom; and'}{'sup': '8', 'sub': 1-6', '1-6, 'Ris a hydrogen atom, Calkyl, or (C) alkyl optionally substituted with a halogen atom.'}5. The method for producing the optically active alcohol compound according to claim 4 , wherein{'sup': 1', '3', '12a', '12b', '12, 'sub': '1-6', 'Ris (C) alkyl optionally substituted with R, or —Si(R)(R)R;'}{'sup': '3', 'sub': '3-8', 'Ris phenyl, or Ccycloalkyl;'}{'sup': 5', '5', '4', '5', '4, 'sub': '4', 'Ris a hydrogen atom, or Roptionally forms a 5-membered ring together with a nitrogen atom to which Rand Rare bonded by forming a Calkylene chain together with R, and in this case the alkylene chain is optionally substituted with an oxo group, or the alkylene chain optionally forms phenyl together with carbon atoms to which two substituents each bond when the two substituents exist at adjacent positions on ...

ISOMETHEPTENE ISOMER

The invention relates to a purified Isometheptene compound comprising the structure according to Formula (I), 4. The compound of claim 2 , wherein the pharmaceutically acceptable addition salt is selected from mucate and bitartrate.5. The compound of claim 2 , wherein the pharmaceutically acceptable addition salt is selected from mucate and bitartrate.6. The compound of claim 3 , wherein the pharmaceutically acceptable addition salt is selected from mucate and bitartrate.7. The (R)-enantiomeric Isometheptene compound of claim 3 , capable of selectively or specifically binding to Imidazoline receptor type 1 (I).8. The (S)-enantiomeric Isometheptene compound of claim 3 , relatively free of binding to Imidazoline receptor type 1 (I).11. A pure (R)-enantiomeric Isometheptene mucate salt according to in crystal form.12. A composition comprising a purified Isometheptene enantiomer or pharmaceutically acceptable addition salt or hydrochloride thereof; and a nontoxic carrier.13. The composition of claim 10 , comprising a purified (S)-Isometheptene enantiomer or hydrochloride or pharmaceutically acceptable addition salt thereof; and a nontoxic carrier.14. The composition of claim 10 , comprising a purified (R)-Isometheptene enantiomer or a hydrochloride or pharmaceutically acceptable addition salt thereof; and a nontoxic carrier.15. A composition comprising a therapeutic amount of the (S)-Isometheptene enantiomer compound of claim 2 , or a pharmaceutically acceptable addition salt thereof; and a nontoxic carrier.16. A composition comprising a therapeutic amount of the (R)-Isometheptene enantiomer compound of claim 3 , or a pharmaceutically acceptable addition salt thereof; and a nontoxic carrier.17. A composition comprising the (S)-Isometheptene enantiomer mucate salt of ; and a nontoxic carrier.18. A composition comprising the (R)-Isometheptene enantiomer mucate salt of ; and a nontoxic carrier.19. The composition according to claim 10 , wherein the Isometheptene enantiomer ...

Device and method for evaluating organic material for organic solar cell

Provided are a novel 1,2-bis(dialkylphosphino)-4,5-(methylenedioxy)benzene derivative that forms a metal complex having particularly high asymmetry induction capacity and catalytic activity on β-dehydroamino acids, a method for manufacturing the same, a metal complex having this 1,2-bis(dialkylphosphino)-4,5-(methylenedioxy)benzene derivative as a ligand, and an asymmetric hydrogenation method using this metal complex. A 1,2-bis(dialkylphosphino)-4,5-(methylenedioxy)benzene derivative represented by general formula (1). (In the formula, R 1 and R 2 represent an alkyl group having 1-10 carbon atoms, and R 1 and R 2 have different numbers of carbon atoms.)

Preparation of sitagliptin intermediates

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

Precatalyst for shibasaki's rare earth metal binolate catalysts

Disclosed herein are schemes for the synthesis of novel hydrogen-bonded rare earth-BINOLate precatalyst complexes, the precatalysts, per se, and their application for the generation of anhydrous REMB catalysts by cation-exchange from metal halides.

PREPARATION METHOD FOR S-INDOXACARB

A catalyst and a method for preparing S-indoxacarb using the catalyst. The catalyst is prepared using 3-tert-butyl-5-(chloromethyl)salicylaldehyde and cyclohexanediamine as raw materials, where an original quinine catalyst such as cinchonine is replaced with the catalyst for application in the asymmetric synthesis of tert-butyl hydroperoxide and 5-chloro-2-methoxycarbonyl-1-indanone ester, greatly improving selection in the asymmetric synthesis process, with the S-enantiomer content increasing from 75% to over 98%, achieving the recycling of a high-efficiency chiral catalyst, and greatly reducing production costs. The synthesis process of the catalyst is simple and is favorable for industrialization, and lays good foundations for the production of high-quality indoxacarb. 2. The preparation method for S-indoxacarb according to claim 1 , comprising the steps of:adding tert-butyl hydroperoxide and 5-chloro-2-methoxycarbonyl-1-indanone ester to the polymerization catalyst solution obtained by the above method to carry out asymmetric synthesis, wherein a mole ratio of 5-chloro-2-methoxycarbonyl-1-indanone ester: 1 tert-butyl hydroperoxide:catalyst is 1:1.2-1.5:0.05-0.1; raising the temperature to 60-120° C. for reflux reaction for 4 hours, filtering the obtained mixture to recover polymer catalyst, the key intermediate 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone is obtained by vacuum distillation of the filtrate, meanwhile, putting the recovered catalyst into toluene solvent to form suspension to continue to participate in the asymmetric synthesis reaction;after obtaining the above-mentioned 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone, making it react with carbobenzoxyhydrazide and diethoxymethane according to the above-mentioned conventional synthesis route, and finally, with hydrogenating deprotection, synthesizing S-indoxacarb with 4-trifluoromethoxy phenyl carbamate.3. The preparation method for S-indoxacarb according to claim 1 , wherein the ...

Method for producing optically active tetrahydroquinolines

Provided are a novel chiral iridium(III) complex; and a method for producing optically active 2-substituted-1,2,3,4-tetrahydroquinolines from 2-substituted-quinolines with the use of the chiral iridium(III) complex through a more economical and easy production process. The disclosed method for producing optically active 2-substituted-1,2,3,4-tetrahydroquinolines comprises reducing a quinoline compound represented by formula [I]: in the presence of a hydrogen donor compound and an iridium (III) complex having a chiral prolinamide compound as a ligand to give an optically active 2-substituted-1,2,3,4-tetrahydroquinoline represented by formula [II]:

NOVEL CHIRAL DIHYDROBENZOOXAPHOSPHOLE LIGANDS AND SYNTHESIS THEREOF

This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands. 15-. (canceled)7. The compound according to wherein{'sup': '1', 'sub': '1-6', 'Ris Calkyl;'}{'sup': 2', '2′, 'Rand R are H;'}{'sup': 3', '4', '5, 'R, R, and Rare H;'}{'sup': 6', '7, 'sub': '1-6', 'Rand Rare Calkyl or aryl;'}and the enantiomers and diastereomers thereof.8. The compound according to wherein{'sup': 6', '7, 'Y is PRR'}{'sup': '1', 'Ris t-butyl;'}{'sup': 2', '2′, 'Rand R are H;'}{'sup': 3', '4', '5, 'R, R, and Rare H;'}{'sup': 6', '7, 'Rand Rare t-butyl or phenyl;'}and the enantiomers and diastereomers thereof.11. The compound according to wherein{'sup': '1', 'sub': 1-6', '3-6, 'Ris Calkyl, Ccycloalkyl or optionally substituted aryl;'}{'sup': 2', '3', '4', '5, 'R, R, R, and Rare each independently selected from H or optionally substituted aryl or heteroaryl;'}{'sup': '6', 'Ris H;'}{'sup': 7', '8, 'sub': '1-6', 'Rand Rare Calkyl;'}{'sup': 9', '10', '11', '12, 'sub': '1-6', 'R, R, Rand Rare independently selected from H and Calkyl;'}and the enantiomers and diastereomers thereof.12. The compound according to wherein{'sup': '1', 'sub': '1-6', 'Ris Calkyl;'}{'sup': 2', '3', '4', '5, 'R, R, R, and Rare H;'}{'sup': '6', 'Ris H;'}{'sup': 7', '8, 'sub': '1-6', 'Rand Rare Calkyl;'}{'sup': 9', '10', '11', '12, 'sub': '1-6', 'R, R, Rand Rare independently selected from H and Calkyl'}and the enantiomers and diastereomers thereof.13. The compound according to wherein{'sup': '1', 'Ris t-butyl;'}{'sup': 2', '3', '4', '3, 'R, R, R, and Rare H;'}{'sup': '6', 'Ris H;'}{'sup': 7', '8, 'Rand Rare methyl;'}{'sup': 9', '10', '11', '12, 'sub': '1-6', 'R, R, Rand Rare independently selected from H and Calkyl'}and the enantiomers and diastereomers thereof.16. The compound according to wherein{'sup': '1', 'sub': 1-6', '3-6, 'Ris Calkyl, Ccycloalkyl ...

NOVEL CHIRAL DIHYDROBENZOOXAPHOSPHOLE LIGANDS AND SYNTHESIS THEREOF

This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands. 2. The compound according to wherein{'sup': '11', 'X is a bond, O, NRor S;'}{'sup': 1', '10, 'sub': 1-6', '3-6, 'Rand Rare each independently selected from Calkyl, Ccycloalkyl or optionally substituted aryl;'}{'sup': 2', '2′', '9', '9′, 'sub': '1-6', 'R, R, Rand R are each independently selected from H, Calkyl, or optionally substituted aryl or heteroaryl;'}{'sup': 3', '4', '5', '6', '7', '8, ', R, R, R, R, Rand Rare each independently selected from H or optionally substituted aryl or heteroaryl;'}and the enantiomers and diastereomers thereof.3. The compound according to whereinX is a bond;{'sup': 1', '10, 'sub': 1-6', '3-6, 'Rand R are each independently selected from Calkyl, Ccycloalkyl, or phenyl;'}{'sup': 2', '2′', '9', '2′, 'R, R, Rand R are each independently selected from H, methyl or isopropyl, phenyl or pyridyl, optionally substituted with methoxy;'}{'sup': 3', '4', '5', '6', '7', '8, 'R, R, R, R, Rand Rare each independently selected from H or phenyl optionally substituted with one or two groups independently selected from methoxy and trifluoromethyl;'}and the enantiomers and diastereomers thereof.4. The compound according to whereinX is a bond;{'sup': 1', '10, 'Rand Rare t-butyl;'}{'sup': 2', '2′', '9', '9′, 'R, R, Rand R are selected from H, methyl and isopropyl; and'}{'sup': 3', '4', '5', '6', '7', '8, 'R, R, R, R, Rand Rare independently selected from phenyl, 3,5-bis(trifluoromethyl)phenyl, 2,6-dimethoxyphenyl or 4-methoxyphenyl;'}and the enantiomers and diastereomers thereof.7. The compound according to wherein{'sup': '1', 'sub': '1-6', 'Ris Calkyl;'}{'sup': 2', '2′, 'Rand R are H;'}{'sup': 3', '4', '5, 'R, R, and Rare H;'}{'sup': 6', '7, 'sub': '1-6', 'Rand Rare Calkyl or aryl;'}and the enantiomers and diastereomers ...

ENANTIOSELECTIVE SYNTHESIS OF ALPHA-QUATERNARY MANNICH ADDUCTS BY PALLADIUM-CATALYZED ALLYLIC ALKYLATION

This invention provides enantioenriched Mannich adducts with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): 163-. (canceled)65. The method of claim 64 , wherein the transition metal catalyst comprises a transition metal selected from palladium claim 64 , nickel claim 64 , and platinum.66. The method of claim 64 , wherein the transition metal catalyst further comprises a chiral ligand.67. The method of claim 64 , wherein the compound represented by formula (Ia) has about 80% ee or greater.68. The method of claim 64 , wherein the compound represented by formula (Ia) has about 85% ee or greater.69. The method of claim 64 , wherein the compound represented by formula (Ia) has about 90% ee or greater. This Application is a Continuation of U.S. patent application Ser. No. 14/972,475, filed Dec. 17, 2015, which claims the benefit of U.S. Provisional Application 62/093,982, filed Dec. 18, 2014, the contents of both of which are incorporated herein by reference.This invention was made with Government support under Grant Number R01GM080269, awarded by the National Institutes of Health. The Government has certain rights in the invention.The Mannich reaction, first discovered in the early 20th century, is among the most robust reactions known to produce nitrogen-containing compounds. In a classic intermolecular Mannich reaction, an aldehyde, an amine and an α-acidic carbonyl compound react to form a β-amino carbonyl compound. Recent progress in this area, including modified imine donors and well-explored catalyst systems, has made available a wide variety of asymmetric α-functionalizations of carbonyl compounds. However, to date, asymmetric Mannich-type reactions to establish α-quaternary carbonyl compounds have been limited to specialized substrate classes.There exists a need for methods that enable access to α-quaternary Mannich Adducts, particularly enantioselective ...

ENANTIOSELECTIVE SYNTHESIS OF alpha-QUATERNARY MANNICH ADDUCTS BY PALLADIUM-CATALYZED ALLYLIC ALKYLATION

This invention provides enantioenriched Mannich adducts with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): 2. (canceled)4. The compound of claim 3 , wherein the sum of m and n is 0 claim 3 , 1 claim 3 , 2 claim 3 , or 3.5. The compound of claim 3 , wherein each occurrence of A claim 3 , B claim 3 , C claim 3 , and D is each independently CR″R′″ or CR″.6. The compound of claim 5 , wherein each occurrence of A claim 5 , B claim 5 , C claim 5 , and D is CR″R′″; andR″ and R′″ are each independently selected for each occurrence from hydrogen, hydroxyl, halogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, (heterocycloalkyl)alkyl, heterocycloalkyl, alkenyl, alkynyl, amino, alkoxy, aryloxy, and alkylamino.7. (canceled)8. The compound of claim 6 , wherein each occurrence of A claim 6 , B claim 6 , C claim 6 , and D is CH.9. The compound of claim 5 , wherein at least two adjacent occurrences of A claim 5 , B claim 5 , C claim 5 , and D are CR″.10. The compound of claim 9 , wherein A and B are each CR″ and m is 1; andR″ is independently selected for each occurrence from hydrogen, hydroxyl, halogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, (heterocycloalkyl)alkyl, heterocycloalkyl, alkenyl, alkenyl, amino, alkoxy, aryloxy, and alkylamino; orthe occurrence of R″ on A and the occurrence of R″ on B are taken together to form an optionally substituted aryl, heteroaryl, cycloalkenyl, or heterocycloalkenyl group.11. (canceled)12. (canceled)13. The compound of claim 3 , wherein at least one occurrence of A claim 3 , B claim 3 , C claim 3 , and D is NR′.14. The compound of claim 13 , wherein at least one occurrence of the remaining A claim 13 , B claim 13 , C claim 13 , and D is NR′ or O.15. The compound of claim 13 , wherein R′ represents independently for each occurrence hydrogen or optionally ...

Novel triglyceride and use thereof

The invention provides a HYA derivative having superior physiological functions intrinsic to HYA and permitting easy ingestion and easy handling, and use thereof. In particular, the invention relates to a triglyceride in which at least one fatty acid forming an ester bond with a hydroxy group of glycerol is 10-hydroxy-cis-12-octadecenoic acid, or an optical isomer thereof, and a composition (edible fat or oil, food, medicament, cosmetic etc.) containing same.

PROCESS

The present invention provides a metallocenyl compound of formula (I). R, R, R, R, R, R, M, m, n, j, k, Y and Z and * are as described in the specification. The invention also provides a process for the preparation of the complexes, a process for increasing the optical purity of a compound of formula (II) and a process for the asymmetric transfer hydrogenation (ATH) of a metallocenyl compound of formula (V) to a metallocenyl compound of formula (IV). 2. The metallocenyl compound according to claim 1 , wherein Ris methyl.3. The metallocenyl compound according to wherein j is 0.4. The metallocenyl compound according to claim 1 , wherein m is 0.5. The metallocenyl compound according claim 1 , wherein n is 0.6. The metallocenyl compound according to claim 1 , wherein Ris methyl and m claim 1 , n and j are 0.7. The metallocenyl compound according to claim 1 , wherein j is 1.8. The metallocenyl compound according to claim 1 , wherein Ris methyl.9. The metallocenyl compound according to claim 1 , wherein Rand Rare methyl.10. The metallocenyl compound according to claim 1 , wherein M is Fe claim 1 , Ru or Os.11. The metallocenyl compound according to claim 1 , wherein Z is selected from the group consisting of a monoatomic anion claim 1 , an oxyanion and an organic anion.12. The metallocenyl compound according to claim 11 , wherein the oxyanion is (HPO) or (HPO).13. The metallocenyl compound according to claim 11 , wherein Z is a monoanion or a dianion.15. The process according to claim 14 , wherein HZ is HPO claim 14 , fumaric acid claim 14 , adipic acid claim 14 , oxalic acid claim 14 , benzoic acid claim 14 , acetic acid claim 14 , methanesulfonic acid and p-toluenesulfonic acid.16. The process according to claim 14 , wherein the solvent is selected from the group consisting of an alcohol claim 14 , an ether claim 14 , an aromatic solvent claim 14 , and an ester or a combination thereof.17. The process according to claim 16 , wherein the solvent is an alcohol.18. The ...

ASYMMETRIC AUXILIARY GROUP

To provide a chiral reagent or a salt thereof. 125-. (canceled)27. The oligonucleotide of claim 26 , wherein Gand Gare taken together to form a heteroatom-containing ring that has 3 to 16 carbon atoms.28. The oligonucleotide of claim 26 , wherein Gand Gare taken together to form a heteroatom-containing ring that has 4 carbon atoms.29. The oligonucleotide of claim 26 , wherein Gis a hydrogen atom claim 26 , a nitro group claim 26 , a halogen atom claim 26 , a cyano group claim 26 , or a group of formula (II) claim 26 , (III) or (V).30. The oligonucleotide of claim 26 , wherein Gis a nitro group claim 26 , a cyano group claim 26 , or a group of formula (II) claim 26 , (III) or (V) claim 26 , or both Gand Gare taken together to form a group of formula (IV).31. The oligonucleotide of claim 26 , wherein Gis a hydrogen atom.32. The oligonucleotide of claim 26 , wherein each of Gand Gis a group of formula (II) claim 26 , wherein Gto Gare independently a hydrogen atom claim 26 , a nitro group claim 26 , a halogen atom claim 26 , a cyano group claim 26 , or Calkyl group.33. The oligonucleotide of claim 26 , wherein each of Gand Gis a group of formula (II) claim 26 , wherein each of Gto Gis a hydrogen atom.34. The oligonucleotide of claim 26 , wherein Gis a group of formula (II) claim 26 , wherein Gto Gare independently a hydrogen atom claim 26 , a nitro group claim 26 , a halogen atom claim 26 , a cyano group or Calkyl group.35. The oligonucleotide of claim 26 , wherein Gis a group of formula (II) claim 26 , wherein each of Gand Gis a hydrogen atom and Gis a nitro group.36. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gto Gare independently Calkyl group claim 26 , Caryl group claim 26 , Caralkyl group claim 26 , Calkyl Caryl group claim 26 , Calkoxy Caryl group claim 26 , or Caryl Calkyl group.37. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gto Gare independently Calkyl group claim 26 ...

Method for producing a spirooxindole derivative

The present disclosure provides a method for efficiently producing and providing compounds having a spirooxindole skeleton, for example compounds having a spirooxindole skeleton and having antitumor activity that inhibit the interaction between Mdm2 protein and p53 protein, or intermediates thereof, using an asymmetric catalyst. Compounds having optically active tricyclic dispiroindole skeletons are obtained through catalytic asymmetric 1,3-dipolar cycloaddition reaction using ketimine as a reaction substrate and using a chiral ligand and a Lewis acid.

Processes for the Preparation of Dasotraline and Intermediates Thereof

The present invention provides processes for the preparation of Dasotraline (1), as well as intermediates useful in the preparation thereof. In particular, processes are provided for the production of the compound of Formula (2), or a salt thereof, and its deprotection to afford Dasotraline (1). 2. The process of claim 1 , wherein Ar is selected from the group consisting of phenyl claim 1 , alkoxy-substituted phenyl claim 1 , alkyl-substituted phenyl claim 1 , and naphthyl.3. The process of claim 2 , wherein Ar is selected from the group consisting of 4-methoxyphenyl and phenyl.4. The process of claim 3 , wherein Ar is 4-methoxyphenyl.5. The process of claim 4 , wherein Ris methyl.6. The process of claim 5 , wherein the deprotection is conducted by acid-mediated hydrolysis comprising treatment of the compound of Formula (2) with an acid selected from the group consisting of trifluoroacetic acid claim 5 , hydrochloric acid claim 5 , and trifluoromethanesulfonic acid.7. The process of claim 6 , wherein the acid is trifluoroacetic acid.8. The process of claim 1 , wherein the carbon atom marked with “*” is enantiomerically enriched in the (S)-configuration and the compound of Formula (2) has a chiral purity in favour of the (1R claim 1 ,4S)-configuration of at least about 90%.10. The process of claim 9 , wherein Ar is selected from the group consisting of phenyl claim 9 , alkoxy-substituted phenyl claim 9 , alkyl-substituted phenyl claim 9 , and naphthyl.11. The process of claim 10 , wherein Ar is selected from the group consisting of 4-methoxyphenyl and phenyl.12. The process of claim 11 , wherein Ar is 4-methoxyphenyl.13. The process of claim 12 , wherein Ris methyl.14. The process of claim 9 , wherein the reductant is selected from the group consisting of sodium borohydride claim 9 , sodium cyanoborohydride claim 9 , and sodium triacetoxyborohydride.15. The process of claim 9 , wherein the carbon atom marked with “*” is enantiomerically enriched in the (S)- ...

Novel tricyclic chiral compounds and their use in asymmetric catalysis

The present invention relates to a compound of general Formula (VIII), the compound having a bowl-shaped conformation, its formation and its use in asymmetric catalysis. In Formula (VIII), M is a metal selected from the group consisting of Group 1 to Group 14 metals, lanthanides and actinides; R is one of —COOR 3 , —R 4 COOR 3 , —R 4 CHO, —R 4 COR 3 , —R 4 CONR 5 R 6 , —R 4 COX, —R 4 OP(═O)(OH) 2 , —R 4 P(═O)(OH) 2 ), —R 4 C(O)C(R 3 )CR 5 R 6 and R 4 CO 2 C(R 3 )O, wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein.

Antifungal Compound Process

The present invention relates to a process for preparing a compound of 5 or 5*, or a mixture thereof, that is useful as an antifungal agent. In particular, the invention seeks to provide new methodology for preparing compounds 7, 7* and 11, 11* and substituted derivatives thereof. 2. The process of claim 1 , further comprising enriching the enantiomeric purity of an enantiomeric compound mixture of Formula 1 and 1* claim 1 , comprising: 'the suitable solvent or solvent mixture is selected from acetonitrile, isopropanol, ethanol, water, methanol, or combinations thereof;', 'crystallizing said enantiomeric compound mixture with a chiral acid in a suitable solvent or solvent mixture, wherein(ii) isolating the enantio-enriched chiral salt mixture; and(iii) free-basing the enantio-enriched chiral salt mixture to provide the enantio-enriched compound mixture.3. The process of claim 2 , further comprising reslurrying the enantio-enriched chiral salt mixture in a slurrying solvent or slurrying solvent mixture.4. (canceled)5. The process of claim 3 , wherein the slurrying solvent or slurrying solvent mixture is a) acetonitrile or b) a mixture of acetonitrile and methanol.6. The process of claim 4 , wherein the mixture of acetonitrile and methanol comprises 80-90% acetonitrile and 10-20% methanol.7. The process of claim 5 , wherein the mixture of acetonitrile and methanol comprises 80-90% acetonitrile and 10-20% methanol.8. The process of claim 2 , wherein the chiral acid is selected from the group consisting of tartaric acid claim 2 , di-benzoyltartaric acid claim 2 , malic acid claim 2 , camphoric acid claim 2 , camphorsulfonic acid claim 2 , ascorbic acid claim 2 , and di-p-toluoyltartaric acid.9. (canceled)11. The process of claim 10 , wherein the mole percent of the chiral catalyst is selected from about 0.5-50 claim 10 , about 0.5-25 claim 10 , about 1-10 claim 10 , and is about 5.1214-. (canceled)15. The process of claim 1 , wherein the number of equivalents of ...

METHOD FOR SYNTHESIZING CHIRAL BETA-HYDROXY ACID ESTER COMPOUND

A method for synthesizing a chiral β-hydroxy acid ester compound is disclosed. The method includes the steps of: using an aldehyde compound and a monoalkyl malonate as raw materials, using a metal and a chiral ligand as a catalyst to make the raw materials be directly and fully reacted in an organic solvent and form a reaction solution, and separating and purifying the reaction solution to obtain the highly stereoselective β-hydroxy acid ester compound. The beneficial effects are mainly embodied in: 1. simple operation; 2. rapidly constructing a highly stereoselective β-hydroxy acid ester skeleton structure molecule; 3. high reaction yield and good stereoselectivity. Therefore, the invention has high basic research significance, industrial production value and social economic benefit. 2. The method according to claim 1 , wherein said organic solvent is selected from one or a combination of dichloromethane claim 1 , ethyl acetate claim 1 , tetrahydrofuran claim 1 , acetonitrile claim 1 , toluene claim 1 , methanol and chloroform.3. The method according to claim 1 , wherein the mass of said organic solvent used is 1-200 times the mass of the raw materials.4. The method according to claim 1 , wherein the molar ratio of said aldehyde compound to said monoalkyl malonate is 1:1-5.5. The method according to claim 1 , wherein said metal compound in said catalyst is selected from the group consisting of one or a combination of copper triflate claim 1 , copper sulfate claim 1 , copper acetate claim 1 , palladium acetate claim 1 , ferrous fluoride claim 1 , silver acetate claim 1 , nickel acetate tetrahydrate claim 1 , nickel acetylacetonate claim 1 , nickel fluoride claim 1 , nickel chloride hexahydrate claim 1 , nickel sulfate claim 1 , nickel perchlorate claim 1 , and bistriphenylphosphine nickel chloride.8. The method according to claim 1 , wherein the ratio of said catalyst to said aldehyde compound is 1 wt %-20 wt % claim 1 , and the molar ratio of the metal to the ...

Method for the stereoselective preparation of amino acid derivatives

The invention relates to a process for the stereoselective preparation of amino acid derivatives, comprising a hydrogenation reaction of the compound of formula (III), alternatively its enantiomer, wherein R is (C 1 -C 8 )-alkyl; followed by a hydrolysis reaction to obtain L-mesityl alanine, alternatively its enantiomer D-mesityl alanine and, optionally, subjecting said compound to an amino group protection reaction, particularly as Fmoc. It also comprises Fmoc-L- or Fmoc-D- mesityl alanine as products per se, useful as intermediates in preparing peptides or peptide analogs with therapeutic or biological activity.

PROCESS FOR THE PREPARATION OF A VIRAL PROTEASE INHIBITOR AND INTERMEDIATES THEREOF

Process for the preparation of a viral protease inhibitor and intermediates useful in its preparation. 2. A process according to wherein a compound of formula (III) wherein R1 is hydrogen is directly converted to a compound of formula (II) by treatment with an oxidising agent selected from the group consisting of potassium permanganate claim 1 , sodium nitrite claim 1 , potassium peroxymonosulphate claim 1 , a mixture of potassium hydrogen sulphate and potassium peroxydisulphate and molecular oxygen in the presence of a copper-based catalyst.5. A process according to further comprising the resolution of the racemic mixture of a compound of formula (II) to give a compound of formula (II) in optically active form claim 1 , wherein R and P are as defined in claim 1 , by enantioselective enzymatic hydrolysis of the ester group of a compound of formula (II) wherein R claim 1 , being as defined above is different from H claim 1 , and P is as defined in .6. A process according to further comprising the resolution of a racemic mixture of a compound of formula (II) to give an enantiomerically pure compound (II) by formation of the diastereomeric salts thereof with a chiral amine.7. A process according to wherein the chiral amine is (S)-1 claim 6 ,2 claim 6 ,3 claim 6 ,4-tetrahydro-1-naphthylamine claim 6 , (S)-phenylethylamine claim 6 , or (S)-naphthylethylamine. The present invention relates to a process for the preparation of a viral protease inhibitor and intermediates useful for its preparation.(1S, 3aR, 6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-[(2-pyrazinylcarbonyl)amino]acetyl]amino-3,3-dimethylbutanoyl]-N-[(1S)-1-[(cyclopropylamino)(oxo)acetyl]butyl]-3,3a,4,5, 6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide of formula (I), also known as telaprevir, is a potent viral protease inhibitor used to treat hepatitis C infections.The preparation of telaprevir, reported in U.S. Pat. No. 7,820,671, involves the assembly of 6 different structural units to create 5 amide bonds ( ...

PARACYCLOPHANE-BASED LIGANDS, THEIR PREPARATION AND USE IN CATALYSIS

A substituted paracyclophane of formula (I) is provided 2. The metal complex according to wherein the metal compound is a compound of palladium (Pd) claim 1 , platinum (Pt) claim 1 , rhodium (Rh) claim 1 , iridium (Ir) or ruthenium (Ru).3. The metal complex according to wherein the substituted paracyclophane (I) is substantially enantiomerically-pure.4. The metal complex according to wherein the metal complex is supported on a solid support.5. The metal complex according to wherein the substituted paracyclophane (I) is substantially enantiomerically-pure.6. A method of asymmetrically hydrogenating a substrate claim 2 , comprising performing the hydrogenation in the presence of a metal complex according to .7. A method of catalyzing a reaction claim 2 , comprising performing the reaction in the presence of a metal complex according to claim 2 , wherein the reaction is selected from the group consisting of carbon-carbon coupling reactions claim 2 , enantioselective isomerization of olefins claim 2 , asymmetric hydroboration reactions claim 2 , asymmetric cyclisation of olefinic aldehydes claim 2 , asymmetric arylation reactions claim 2 , asymmetric alkylation reactions and amination of aryl halides (Hartwig-Buchwald reaction). This application is a Division of U.S. patent application Ser. No.12/675,918, filed Oct. 22, 2010, which is the U.S. National Phase filing of PCT International Application No. PCT/GB2008/050730, filed Aug. 21, 2008, and claims priority of British Patent Application No. 0716714.1, filed Aug. 29, 2007, the disclosures of which applications are incorporated herein by reference in their entirety.This invention relates to ligands used in transition metal-catalysed reactions and in particular to substituted paracyclophanes.Paracyclophanes and in particular [2.2]-paracyclophane derivatives are established ligands for transition metal-catalysed asymmetric reactions (see for example, S. E. Gibson and J. D. Knight, 2003, 1, 1256-1269). Of these, ...

METHOD OF PRODUCING PROTON PUMP INHIBITOR COMPOUND HAVING OPTICAL ACTIVITY

A highly pure optically active proton pump inhibitor compound can be produced safely and inexpensively in a high yield and enantioselectivity by a method of producing an optically active sulfoxide of Formula 2 or a salt thereof, comprising oxidizing a sulfide of Formula 1 or a salt thereof with hydrogen peroxide using an iron salt in the presence of a chiral ligand of Formula 3; wherein A is CH or N; Ris hydrogen atom, an alkyl optionally substituted by halogen(s), or an alkoxy optionally substituted by halogen(s); one to three Rmay exist, and each of Ris independently an alkyl, a dialkylamino, or an alkoxy optionally substituted by halogen(s) or alkoxy(s); each of Ris independently hydrogen atom, a halogen, cyano or the like; Ris a tertiary alkyl; and * and ** represent respectively R configuration or S configuration. 15-. (canceled) The present invention relates to a process of producing an optically active proton pump inhibitor compound. More specifically, the present invention relates to a method of producing an optically active proton pump inhibitor compound comprising asymmetric oxidation using an iron salt in the presence of a chiral ligand.Proton pump inhibitor is a drug that acts on proton pumps in parietal cells in stomach, and inhibits secretion of gastric acid. Proton pump inhibitor is useful for treating gastric ulcer, duodenal ulcer, anastomotic ulcer, reflux esophagitis, non-erosive gastroesophageal reflux disease or Zollinger-Ellison syndrome, and for sterilization supplement for in gastric ulcer, duodenal ulcer, gastric MALT lymphoma, idiopathic thrombocytopenic purpura, remnant stomach after endoscopic submucosal dissection for early gastric cancer, or gastritis, and the like. As a proton pump inhibitor compound, a benzimidazole-type or imidazopyridine-type compound or the like are known, as represented by, for example, omeprazole, esomeprazole, lansoprazole, rabeprazole, tenatoprazole, pantoprazole, reminoprazole, dexlansoprazole, which are shown ...

METHOD FOR PRODUCING OPTICALLY ACTIVE PYRROLIDINE COMPOUNDS

The present invention provides a process for preparing a compound represented by formula (VII), which comprises reacting a compound represented by formula (VI) with a malonic acid derivative in the presence of a base and an asymmetric catalyst in a two layer solvent system of hydrophobic solvent and water.

Methods for asymmetric e poxidation using flow reactors

Embodiments of the present disclosure relate to asymmetric epoxidation of olefinic alcohols, using a chiral alcohol chelated titanium catalyst and an organic peroxide performed in a microreactor flow reactor system that can comprise multiple microreactor modules. Molecular sieves can be used to remove any adventitious water in the reagent feed solutions and ensure an anhydrous reaction solution. The use of a microreactor flow reactor allows for the epoxidation reaction to be run at elevated temperatures of at least 20, 30, or even 50° C., which dramatically accelerates the reaction, but without a large drop in enantioselectivity. The reaction can therefore be performed with short reaction times resulting in a high throughput.

Asymmetrical hydrogenation reaction of ketonic acid compound

The present invention relates to the technical field of organic chemistry, specifically an asymmetrical hydrogenation of an ∂-ketonic acid compound, the technical proposal being as shown by the following formula: 2. The preparation method according to claim 1 , wherein claim 1 , the molar dosage ratio of the said base to the substrate A compound is (1.001∥1.5):1.3. The preparation method according to claim 1 , wherein claim 1 , Ris a phenyl claim 1 , a substituted phenyl claim 1 , a naphthyl or a substituted naphthyl.4. The preparation method according to claim 1 , wherein claim 1 , R is 4-Bu.5. The preparation method according to claim 1 , wherein claim 1 , the said base is sodium hydroxide or potassium hydroxide.6. The preparation method according to any claims of 1 claim 1 , 3-5 claim 1 , wherein claim 1 , under the protection of nitrogen atmosphere claim 1 , at a hydrogen pressure of 0.5-10 MPa claim 1 , with a base dosage 1.0˜3.0 molar equivalent claim 1 , in the presence of organic solvent claim 1 , ∂-ketonic acid compound is formed into B compound in the catalytic of chiral spiro-pyridylamidophosphine ligand iridium complex (M) with the molar dosage 0.00001˜0.01 molar equivalent.7. The preparation method according to any claims of 1 claim 1 , 3-5 claim 1 , wherein claim 1 , under the protection of nitrogen atmosphere claim 1 , were added into the inner hydrogenation tube substrate A claim 1 , 1.0˜3.0 molar equivalent base claim 1 , chiral spiro-pyridylamidophosphine ligand iridium complex (M) with the molar dosage 0.00001˜0.01 molar equivalent and the solvent; The inner reaction tube was placed into the hydrogenation reactor at a hydrogen pressure of 0.5-10 MPa was filled; The reaction was stirred for 1-30 hours at a temperature of 10˜90° C. to obtain B compound; the base selected from sodium hydroxide claim 1 , potassium hydroxide claim 1 , sodium tert-butyl oxide or potassium tert-butyl oxide.8. The preparation method according to claim 1 , wherein claim 1 ...

Antifungal compound process

The present invention relates to a process for preparing a compound of 5 or 5*, or a mixture thereof, and/or a compound of 14 or 14*, or a mixture thereof, that is useful as an antifungal agent. In particular, the invention seeks to provide new methodology for preparing compounds 7, 7* and 11, 11* and substituted derivatives thereof.

SOLID-SUPPORTED RUTHENIUM-DIAMINE COMPLEXES, AND METHODS FOR PRODUCING OPTICALLY ACTIVE COMPOUNDS

Provided is a solid-supported ruthenium complex represented by general formula (1), (2) or (3). Further provided are: a method for manufacturing a reduction product by reducing an organic compound in the presence of the solid-supported ruthenium complex and a hydrogen donor; a method for manufacturing an optically active alcohol, characterized by reducing a carbonyl group in a carbonyl compound in the presence of the solid-supported ruthenium complex and a hydrogen donor; and a method for manufacturing an optically active amine, characterized by reducing an imino group of an imine compound in the presence of the solid-supported ruthenium complex and a hydrogen donor. 110-. (canceled)12. A method for producing a reduction product , comprising{'claim-ref': {'@idref': 'CLM-00011', 'claim 11'}, 'reducing an organic compound in the presence of the solid-supported ruthenium complex according to and a hydrogen donor.'}13. A method for producing an optically active alcohol , comprising{'claim-ref': {'@idref': 'CLM-00011', 'claim 11'}, 'reducing a carbonyl group of a carbonyl compound in the presence of the solid-supported ruthenium complex according to and a hydrogen donor.'}14. A method for producing an optically active amine , comprising{'claim-ref': {'@idref': 'CLM-00011', 'claim 11'}, 'reducing an imino group of an imine compound in the presence of the solid-supported ruthenium complex according to and a hydrogen donor.'}15. The method for producing a reduction product according to claim 12 , wherein the hydrogen donor is selected from the group consisting of formic acid claim 12 , alkali metal formates claim 12 , and alcohols having a hydrogen atom at an α-position carbon atom of a hydroxyl-bearing carbon.16. The method for producing an optically active alcohol according to claim 13 , wherein the hydrogen donor is selected from the group consisting of formic acid claim 13 , alkali metal formates claim 13 , and alcohols having a hydrogen atom at an α-position carbon ...

Method for producing 2-pyridone compound

To provide a method for producing a compound represented by the formula (1) which is a 2-pyridone compound useful as a pharmaceutical or an intermediate for a pharmaceutical, etc. at a high yield. A method for producing a 2-pyridone compound represented by the formula (1), which comprises reacting a 6-benzoyl-2-pyridone compound represented by the formula (3) with a sulfone compound represented by the formula (4):

METHOD FOR THE INDUSTRIAL PRODUCTION OF 2-HALO-4,6-DIALKOXY-1,3,5-TRIAZINES AND THEIR USE IN THE PRESENCE OF AMINES

A method for stabilization of collagen matrices and of condensation of natural and synthetic polymers that uses 2-halo-4,6-dialkoxy-1,3,5-triazines in the presence of one or more amines as activating agents for reactions of crosslinking, condensation, grafting, and curing of collagen matrices, cellu lose, modified celluloses, polysaccharides, acid unsaturated polymers, and chiral and non-chiral amines, etc. Forming an integral part of the present invention is also the method for production on an industrial scale of 2-halo-4,6-dialkoxy-1,3,5-triazines. 137-. (canceled)39. The method according to claim 38 , wherein the first reagent comprises one or more 2-halo-4 claim 38 ,6-dialkoxy-1 claim 38 ,3 claim 38 ,5-triazines of formula III as active principle claim 38 , in a concentration ranging between 0.1 and 1.0 M.40. The method according to claim 38 , wherein Reagent 1 comprises a buffer selected from the group consisting of MES claim 38 , ACES claim 38 , BES claim 38 , BIS-Tris claim 38 , MOPS claim 38 , TEA claim 38 , TAPSO claim 38 , POPSO claim 38 , TAPS claim 38 , formiate claim 38 , phosphate claim 38 , and succinate; and a base or a salt of formula XY claim 38 , where X is selected from the group consisting of Na claim 38 , K claim 38 , and Ag claim 38 , and Y is selected from the group consisting of ClO claim 38 , BF claim 38 , PF claim 38 , CO claim 38 , Cl claim 38 , and HCO.41. The method according to claim 38 , wherein the solvent of Reagent 1 is selected from the group consisting of aliphatic ether claim 38 , halogenate claim 38 , alcohol claim 38 , ketone claim 38 , ester claim 38 , aromatic hydrocarbon claim 38 , aliphatic hydrocarbon claim 38 , amide claim 38 , carbonate claim 38 , DMSO claim 38 , and water.42. The method according to claim 38 , wherein Reagent 2 comprises one or more linear claim 38 , branched claim 38 , cyclic claim 38 , aromatic claim 38 , heterocyclic tertiary amines claim 38 , and/or a quaternary salt thereof as active principle ...

METHOD FOR PREPARING (R)-PRAZIQUANTEL

The invention relates to a new method for preparing (R)-praziquantel. In the invention, by taking advantage of the high stereo selectivity, site selectivity and region selectivity of an enzyme, an intermediate of a pure optical and chiral (R)-praziquantel are obtained by means of the dynamic kinetic resolution of an enantiomer from the synthesized racemate or derivatives thereof, and the (R)-praziquantel is obtained by using various conventional and mature organic chemical reactions with higher yield. The method of the invention has the potential advantages of easily available raw materials, low cost, environmentally safer process and convenience for large-scale production. Also, the purity of the end product can be more than 98%. By adopting the invention, the quality of the product is improved and a basis for developing high quality of active pharmaceutical ingredients and formulations is established, and thus the pending industrial problem of purifying praziquantel over 30 years becomes solvable. 2Candida RugosaCandida AntarcticaCandida Antarctica. The method for preparing (R)-praziquantel as claimed in claim 1 , wherein the lipase is selected from the group consisting of Lipase claim 1 , Lipase A and Lipase B.3. The method for preparing (R)-praziquantel as claimed in claim 1 , wherein R is selected from the group consisting of methyl claim 1 , ethyl claim 1 , isopropyl claim 1 , tert-butyl and p-methoxyphenyl.4. The method for preparing (R)-praziquantel as claimed in claim 1 , wherein the racemic compound 3e is reacted with the lipase in a water-saturated ionic liquid in the presence of a base at 0-50° C. claim 1 , to obtain compound 4.5. The method for preparing (R)-praziquantel as claimed in claim 4 , wherein the ionic liquid is selected from the group consisting of 1-n-butyl-3-methylimidazolium tetrafluoroborate claim 4 , 1-n-butyl-3-methylimidazolium hexafluorophosphate claim 4 , 1-n-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide and 1-n-butyl ...

Identification of NSC23925 Isomers to Reverse Multidrug Resistance in Human Cancers

This disclosure features optically active stereoisomers of (2-(4-methoxy)quinolin-4-yl)(piperidin-2-yl)methanol that reduce drug resistance, compositions containing the same, and methods of using and preparing the same.

ALUMINUM CATALYST

An aluminum catalyst is obtained by reacting at least one compound of a specific alkylaluminum compound and a specific hydridoaluminum compound with a specific hydroxy compound. The specific hydroxyl compound is a specific 2-cycloalkyl-6-arylphenol or a specific di(2-cycloalkyl-6-arylphenol). A method for producing isopulegol or optically active isopulegol includes selectively cyclizing citronellal using the aluminum catalyst. The present invention relates to an organoaluminum compound obtained by reacting at least one aluminum compound selected from an alkylaluminum and a hydridoaluminum with at least one of phenol compounds selected from a 2-cycloalkyl-6-arylphenol and a di(2-cycloalkyl-6-arylphenol).The present invention further relates to a method for producing isopulegol by cyclizing citronellal with high n-selectivity using the organoaluminum compound as a catalyst.Conventionally, menthol, particularly L-menthol, is very important as flavor or fragrance having fresh-feeling and its use is very wide. As synthesis methods of L-menthol, a method of obtaining it by optical resolution of DL-menthol and a method of obtaining L-menthol by an asymmetric synthesis method are known. In the production step of L-menthol by the asymmetric synthesis method, L-menthol is obtained by hydrogenating L-isopulegol which is a precursor. However, in order to synthesize the L-isopulegol, a high selective cyclization reaction of D-citronellal is an important step.As the selective cyclization reaction of D-citronellal, the disclosed method, that is, the production of L-isopulegol using zinc bromide as a catalyst, was already performed (Patent Document 1). In this case, the ratio of L-isopulegol to other isomers is about 90% as diastereoselectivity.A selective cyclization reaction of citronellal by an aluminum siloxide catalyst has been reported (Patent Documents 2 and 3). In this case, the diastereoselectivity of isopulegol formed is up to 96%.Selective cyclization reactions of D- ...

PICOLINAMIDES AS FUNGICIDES

This disclosure relates to picolinamides of Formula I and their use as fungicides. 3. The compound according to claim 2 , wherein Rand Rare independently chosen from hydrogen or alkyl.4. The compound according to claim 2 , wherein Ris aryl claim 2 , optionally substituted with 0 claim 2 , 1 or multiple R.5. The compound according to claim 2 , wherein Rand Rare independently chosen from hydrogen or alkyl claim 2 , and Ris aryl claim 2 , optionally substituted with 0 claim 2 , 1 or multiple R.7. The compound according to claim 6 , wherein Rand Rare independently chosen from hydrogen or alkyl.8. The compound according to claim 6 , wherein Ris aryl claim 6 , optionally substituted with 0 claim 6 , 1 or multiple R.9. The compound according to claim 6 , wherein Rand Rare independently chosen from hydrogen or alkyl claim 6 , and Ris aryl claim 6 , optionally substituted with 0 claim 6 , 1 or multiple R.11. The compound according to wherein Z is N.12. The compound according to wherein W is O.13. The compound according to claim 12 , wherein Ris alkoxy.14. The compound according to claim 13 , wherein Ris hydrogen.15. The compound according to claim 14 , wherein Rand Rare independently chosen from hydrogen or alkyl.16. The compound according to claim 14 , wherein Ris aryl claim 14 , optionally substituted with 0 claim 14 , 1 or multiple R.17. The compound according to claim 14 , wherein Rand Rare independently chosen from hydrogen or alkyl claim 14 , and Ris aryl claim 14 , optionally substituted with 0 claim 14 , 1 or multiple R.18. The compound according to claim 13 , wherein Ris chosen from —C(O)Ror —CHOC(O)R.19. The compound according to claim 18 , wherein Rand Rare independently chosen from hydrogen or alkyl.20. The compound according to claim 18 , wherein Ris aryl claim 18 , optionally substituted with 0 claim 18 , 1 or multiple R.21. The compound according to claim 18 , wherein Rand Rare independently chosen from hydrogen or alkyl claim 18 , and Ris aryl claim 18 , ...

Method for producing optically active valeric acid derivative

A method for producing a compound (3), which comprises allowing a compound (1) to react with hydrogen gas in an inert solvent, in the presence of a specific chiral ligand and a ruthenium catalyst, or in the presence of an asymmetric transition metal complex catalyst previously generated from the chiral ligand and the ruthenium catalyst.

Process for producing alcohol analogue

Provided is a process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde. The process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde is characterized by reacting an aldehyde or an imine with a boric acid enol ester in the presence of a copper compound and an optically active bidentate phosphine compound.

SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery. 2. The compound of claim 1 , wherein Ris selected from the group consisting of CHPh claim 1 , CHO-t-Bu claim 1 , CHCHCH claim 1 , CH(1-Naph) claim 1 , CHOH claim 1 , CHOCHPh claim 1 , and CHOCH(α-Me-CH) claim 1 , or Ris selected from the group consisting of OR′ (where R′ is an ester or alkyl group) claim 1 , CH claim 1 , an alkyl group claim 1 , CHOH claim 1 , and the other of Rand Ris H or OH claim 1 , and n is greater than 250.3. The compound of claim 1 , wherein said compound has a molecular weight of at least 50 claim 1 ,000.4. A chiral substituted polyvinylpyrrolidinone compound comprising an acetonide moiety attached to the pyrrolidine ring.6. A complex comprising the chiral substituted polyvinylpyrrolidinone compound of bound to a core species selected from the group consisting of nanoparticulate materials claim 1 , proteins claim 1 , DNA claim 1 , siRNA claim 1 , and dsRNA.7. The complex of claim 6 , wherein the complex comprises a nanoparticle cluster.8. The complex of claim 7 , wherein the nanoparticle cluster comprises one or more metals.9. The complex of claim 8 , wherein the nanoparticle cluster comprises one or more metals selected from the group consisting of Au claim 8 , Pd claim 8 , Cu claim 8 , Ce claim 8 , Mo claim 8 , Ni claim 8 , Ru claim 8 , W claim 8 , and Fe.10. The complex of claim 8 , wherein the nanoparticle cluster is bimetallic.11. The complex of claim 6 , wherein the bimetallic nanoparticle cluster is selected from the group consisting of Pd/Au ...

METHOD FOR PRODUCING A SPIROOXINDOLE DERIVATIVE

The present disclosure provides a method for efficiently producing and providing compounds having a spirooxindole skeleton, for example compounds having a spirooxindole skeleton and having antitumor activity that inhibit the interaction between Mdm2 protein and p53 protein, or intermediates thereof, using an asymmetric catalyst. Compounds having optically active tricyclic dispiroindole skeletons are obtained through catalytic asymmetric 1,3-dipolar cycloaddition reaction using ketimine as a reaction substrate and using a chiral ligand and a Lewis acid. 3. The method of claim 2 , wherein the Lewis acid is a Cu(I) Lewis acid or a Cu(II) Lewis acid.4. The method of claim 2 , wherein the Lewis acid is selected from the group consisting of CuOAc claim 2 , CuCl claim 2 , CuBr claim 2 , CuI claim 2 , CuOTf claim 2 , CuPF claim 2 , CuBF claim 2 , Cu(OAc) claim 2 , Cu(OTf) claim 2 , and CuSO.5. The method of claim 2 , whereinthe chiral ligand selected from the group consisting of a compound of formula (VI), a compound of formula (VII), a compound of formula (VIII), a compound of formula (IX), a compound of formula (X), a compound of formula (XI), and a compound of formula (XII),{'sup': '6', 'Ris a phenyl group optionally substituted with 1 to 3 substituents independently selected from the group consisting of a methyl group, a t-butyl group, and a methoxy group,'}ring Y is a benzene ring, a cyclohexane ring, or a dioxolane ring,{'sup': '7', 'Ris a phenyl group or a furanyl group, wherein'}the phenyl group and the furanyl group are each optionally substituted with 1 to 3 substituents independently selected from the group consisting of a methyl group, a t-butyl group, and a methoxy group,{'sup': '8', 'Ris a hydrogen atom or a methoxy group,'}{'sup': '9', 'Ris a methoxy group, or,'}{'sup': '9', 'two Rmoieties together form a 9-membered heterocyclic ring containing two oxygen atoms in the ring,'}{'sup': '10', 'Ris a methoxy group,'}{'sup': '11', 'sub': '2', 'V is P(R),'}{'sup': ' ...

Pd(II)-catalyzed Enantioselective Beta-Methylene C(sp3)–H Bond Activation

Chiral acetyl-protected aminoethyl quinoline (APAQ), pyridine and imazoline ligands are disclosed that enable Pd (II)-catalyzed enantioselective arylation or heteroarylation of ubiquitous prochiral β-methylene C—H bonds of aliphatic amides offers an alternative disconnection for constructing β-chiral centers. Systematic tuning of the ligand structure reveals that a six-membered instead of a five-membered chelation of these types of ligands with the Pd(II) is important for accelerating the C(sp)-H activation thereby achieving enantioselectivity for quinoline and pyridine ligands. 2. The compound according to claim 1 , wherein E is CH that is part of a double bond.3. The compound according to claim 2 , wherein n is one.4. The compound according to claim 3 , wherein said Ring contains two fused rings that each contains 6 atoms.5. The compound according to claim 1 , wherein Z is oxygen.6. The compound according to claim 5 , wherein n is zero.7. The compound according to claim 6 , wherein said Ring contains one ring that contains five ring atoms.8. The compound according to claim 1 , Ris a straight chain C-Chydrocarbyl group claim 1 , or a C-Chydrocarbyloxy group.9. The compound according to claim 1 , wherein Ris phenyl claim 1 , Rand Rare the same substituent claim 1 , and are bonded a) in the 3- and 5-positions or b) in the 2- and 6-positions.10. The compound according to claim 9 , wherein Rand the phenyl ring containing Rand Rsubstituents are in a syn or anti relationship.12. The compound according to claim 11 , wherein Ris phenyl claim 11 , Rand Rare the same substituent claim 11 , and are bonded a) in the 3- and 5-positions or b) in the 2- and 6-positions.13. The compound according to claim 12 , wherein Rand the phenyl ring containing Rand Rsubstituents are in a syn or anti relationship.14. The compound according to claim 13 , wherein Rand Rare t-butyl.15. The compound according to claim 14 , wherein said compound corresponds in structure to Formula A-1.16. The ...

SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME

A compound represented by a formula [1D] as shown below (wherein R 1A , R 1B , R 2A , R 2B , R 3A and R 3B represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, and the like) is useful as an intermediate for producing a thionucleoside, and the production method of the present invention is useful as a method for producing a thionucleoside.

Kinetic resolution of racemic hydroxy ester via asymmetric catalytic hydrogenation and application thereof

The present invention relates to kinetic resolution of racemic δ-hydroxyl ester via asymmetric catalytic hydrogenation and an application thereof. In the presence of chiral spiro pyridyl phosphine ligand Iridium catalyst and base, racemic δ-hydroxyl esters were subjected to asymmetric catalytic hydrogenation to obtain extent optical purity chiral δ-hydroxyl esters and corresponding 1,5-diols. The method is a new, efficient, highly selective, economical, desirably operable and environmentally friendly method suitable for industrial production. An optically active chiral δ-hydroxyl ester and 1,5-diols can be obtained at very high enantioselectivity and yield with relatively low usage of catalyst. The chiral δ-hydroxyl ester and 1,5-diols obtained by using the method can be used as a critical raw material for asymmetric synthesis of chiral drugs (R)-lisofylline and natural drugs (+)-civet, (−)-indolizidine 167B and (−)-coniine. 3. The kinetic resolution method of racemic δ-hydroxyl esters via asymmetric catalytic hydrogenation according to claim 1 , wherein claim 1 , Ris C˜Calkyl claim 1 , phenyl claim 1 , cyclopentyl tert-butyloxyl methyl.4. The kinetic resolution method of racemic -hydroxyl esters via asymmetric catalytic. hydrogenation according to or claim 1 , wherein claim 1 , the said racemic δ-hydroxyl esters also included δ-hydroxyl lactone esters.8. The kinetic resolution method of racemic δ-hydroxyl esters via asymmetric catalytic hydrogenation according to claim 2 , wherein claim 2 , in the presence of organic solvent claim 2 , were added δ-hydroxyl esters claim 2 , catalysts claim 2 , base; the reaction mixture was stirred for 0.5-24 h to react at the hydrogen atmosphere 1-100 atm to obtain optical active chiral δ-hydroxyl esters and corresponding chiral 1 claim 2 ,5-diols.9. The kinetic resolution method of racemic δ-hydroxyl esters via asymmetric catalytic hydrogenation according to - claim 2 , wherein claim 2 , the said base is alcohol alkalis claim 2 , ...

METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND, AND NOVEL METAL-DIAMINE COMPLEX

The present invention pertains to a method for producing an optically active compound which includes a step for reducing an imino group of an imine compound or a step for reducing an unsaturated bond of a heterocyclic compound, while in the presence of hydrogen gas as a hydrogen donor and one or more types of complexes selected from a group consisting of a complex represented by general formula (1), a complex represented by general formula (2), a complex represented by general formula (3), and a complex represented by general formula (4) (the general formulas (1)-(4) are as stipulated by claim ). 4. An asymmetric reduction catalyst comprising the complex according to .5. An asymmetric reduction catalyst comprising the complex according to . The present invention relates to a method for selectively producing an optically active compound important as a precursor for synthesis of pharmaceuticals and functional materials, the methods using any of a ruthenium-diamine complex, an iridium-diamine complex, and a rhodium-diamine complex as a catalyst.In the field of production of optically active amines, many asymmetric reactions, including asymmetric reduction, have been developed, and many asymmetric reactions have been reported which use asymmetric metal complexes having optically active phosphine ligands. Meanwhile, for example, there are many documents reporting that complexes in each of which an optically active nitrogen compound is coordinated to a transition metal, such as ruthenium, rhodium, or iridium, have excellent performance as catalysts for asymmetric synthesis reactions (see Chem Rev. (1992), p. 1051, J. Am. Chem. Soc. 117 (1995), p. 7562, J. Am. Chem. Soc. 118 (1996), p. 2521, and J. Am. Chem. Soc. 118 (1996), p. 4916). Especially, synthesis of optically active amines by hydrogenation reaction has been reported recently (see J. Am. Chem. Soc. 133 (2011), p. 9878, and Angew. Chem. Int. Ed 51 (2012), p. 5706).However, the conventional asymmetric synthesis ...

SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME

A compound represented by a formula [1D] as shown below (wherein R 1A , R 1B , R 2A , R 2B , R 3A and R 3B represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, and the like) is useful as an intermediate for producing a thionucleoside, and the production method of the present invention is useful as a method for producing a thionucleoside.

COMPOUND AND METHOD FOR MANUFACTURING ORGANIC MATERIAL

Synthesis of organic compounds that has chirality is an important technique in the fields of pharmaceuticals, agrichemicals, health foods and the like. However, raw materials of a catalyst used for the synthesis of such compounds are expensive, and the synthesis needs many steps, so that it is difficult to reduce the cost. Linking a catalyst center to a polymer chain or a resin through an organic group enables to use the catalyst repeatedly and produce a chiral compound at low cost. 1. A compound comprising:a plurality of first portions;a second portion; anda linker that connects each of the plurality of first portions with the second portion and that has at least one covalent bond,wherein each of the plurality of first portions has a chirality;the chirality is induced by any one selected from the group consisting of an asymmetric atom, an axial chirality, a planar chirality and a helix; each of the plurality of first portions has a first atom that bonds directly to the asymmetric atom, and', 'the linker bonds directly to the first atom;, 'when the chirality is induced by the asymmetric atom,'} each of the plurality of first portions has an axially chiral substituent to be the axial chirality,', 'the linker bonds directly to: a second atom contained in a cyclic structure that shares a plurality of atoms in constituent atoms that constitutes the axially chiral substituent; or a third atom contained in the axially chiral substituent, and', 'a bond between: a fourth atom; and the second atom or the third atom is rotatable, the fourth atom being contained in the linker and bonding directly to the second atom or the third atom;, 'when the chirality is induced by the axial chirality,'} the compound has a planar-chiral substituent to be the planar chirality,', 'the linker bonds directly to a fifth atom contained in the planar-chiral substituent, and', 'a bond between a sixth atom and the fifth atom is rotatable, the sixth atom being contained in the linker and bonding ...

Compound having chiral spirobiindane skeleton and preparation method therefor

Chiral spirobiindane skeleton compound and preparation method thereof is disclosed in the present invention. The spirobiindane skeleton compound of the present invention having the structure formula of I or I′; the preparation method for synthesizing the spirobiindane skeleton compound of the present invention comprising the following steps: in the presence of solvent and catalysts, the structure formula compound III reacted through intramolecular Friedel-Crafts reaction to obtain the compound of formula I; the catalyst is a Browsteric acidor Lewis acid. The preparation method of chiral fused spirobiindane skeleton compound of the present invention does not need to adopt chiral starting materials or chiral resolving agents, does not require chiral resolving steps, is simple in method, is simple in post-treatment, and is economic and environment friendly. High product yield, high product optical purity and chemical purity. The catalyst for the asymmetric reaction is obtained from the chiral spirobiindane skeleton ligand of the present invention, under the catalytic reagent of transition metal, the catalyzed hydrogenation reaction can arrive at a remarkable catalytic effect with a product yield of >99%, and a product ee value of up to >99%. 2. The compound of claim 1 , comprising:{'sup': 1', '8', '2', '7', '3', '6, 'Rand Rare the same; and/or, Rand Rare the same; and/or, Rand Rare the same;'}{'sup': 4', '5, 'and/or, Rand Rare the same; and/or, n=0, 1, 2 or 3.'}3. The compound of or claim 1 ,wherein claim 1 ,{'sup': 1', '2', '3', '4', '5', '6', '7', '8, 'sub': 1', '10', '1', '10', '1', '6, 'R, R, R, R, R, R, Rand Rare each independently C˜Calkyl, the C˜Calkyl is C˜Calkyl;'}{'sup': 1', '2', '3', '4', '5', '6', '7', '8, 'sub': 3', '10', '3', '10', '3', '6, 'R, R, R, R, R, R, Rand Rare each independently C˜Ccycloalkyl, the C˜Ccycloalkyl is C˜Ccycloalkyl;'}{'sup': 1', '2', '3', '4', '5', '6', '7', '8, 'sub': 1', '4', '1', '4', '1', '3, 'R, R, R, R, R, R, Rand Rare each ...

METHOD FOR THE INDUSTRIAL PRODUCTION OF 2-HALO-4,6-DIALKOXY-1,3,5-TRIAZINES AND THEIR USE IN THE PRESENCE OF AMINES

A method for stabilization of collagen matrices and of condensation of natural and synthetic polymers that uses 2-halo-4, 6-dialkoxy-1, 3, 5-triazines in the presence of one or more amines as activating agents for reactions of crosslinking, condensation, grafting, and curing of collagen matrices, cellulose, modified celluloses, polysaccharides, acid unsaturated polymers, and chiral and non-chiral amines, etc. Forming an integral part of the present invention is also the method for production on an industrial scale of 2-halo-4, 6-dialkoxy-1, 3, 5-triazines. 137-. (canceled)39. The method according to claim 38 , wherein the substitution reaction is conducted at a temperature of between 45° C. and 135° C. for a time comprised between 5 h and 48 h.40. The method according to claim 38 , wherein the quenching of the reaction by adding water and stirring has a duration ranging between 0 min and 480 min.41. The method according to claim 38 , wherein the reagents are added in the reactor in which the reaction is carried out in the following order:6-7.9 Eq of base together with 4-4.1 Eq of alcohol and 7.7-10 Eq of water;{'sub': 3', '3', '3, 'sup': −', '−, '1 Eq of cyanuric trihalogenide CNX, where X is Br or Cl (compound of formula I) over 0.5-3 h under vigorous stirring.'}42. The method according to claim 38 , wherein the aliphatic alcohol is methanol claim 38 , ethanol claim 38 , isopropanol claim 38 , or butanol.43. The method according to claim 38 , which is conducted on an industrial scale in a batch reactor with an ellipsoidal bottom claim 38 , wherein the batch reactor is pressure resistant claim 38 , reinforced claim 38 , lined with steel claim 38 , and equipped with means for the addition of reagents claim 38 , means for stirring claim 38 , and means for temperature control.45. The method according to claim 44 , wherein the first reagent comprises one or more 2-halo-4 claim 44 ,6-dialkoxy-1 claim 44 ,3 claim 44 ,5-triazines of formula III as active principle claim 44 ...

CHIRAL COMPOUNDS OF VARYING CONFORMATIONAL RIGIDITY AND METHODS OF SYNTHESIS

Synthesis of compounds having varying degrees of conformational rigidity is obtained via a low cost, high yield and efficient synthetic reactions. The library of compounds is structurally diverse, having at least one or more chiral centers and providing large numbers of compounds having building block diversity and substantial scaffold diversity. The compounds further provide a novel method for obtaining candidate therapeutic agents for prevention, treatment or diagnosis of diseases. 2. The method of claim 1 , wherein Rand Rcomprise a molecular architecture compatible with the synthesis of Formula I′ or introduced after synthesis of a central pentenoic acid of Formula I′.3. The method of claim 1 , wherein two or more monomers of Formula I′ are optionally oligomerized claim 1 , the oligomerization of Formula I′ proceeding via a 1- or 2-directional homologation or functionalization of Formula I′.4. The method of claim 3 , wherein X and Y comprise any molecule compatible with the oligomerization of Formula I′.5. The method of claim 2 , wherein an oligomer or polymer of Formula I′ comprises homogeneous monomers claim 2 , heterogeneous monomers or combinations thereof.7. The compound of claim 6 , wherein an oligomeric compound comprises at least two or more monomers represented by Formula I comprising a chiral center in an R configuration claim 6 , an S configuration or multiple combinations thereof.8. The compound of claim 6 , wherein the monomer of Formula I is a pentenoic amide.9. The compound of claim 8 , wherein the pentenoic amide is a central N-substituted 5-amino-2 claim 8 , 4-dialkyl-3-pentenoic amide.10. The compound of claim 6 , wherein a monomer of Formula I comprises substitutions which maintain conformational control about a β claim 6 , γ-unsaturated carbonyl and minimize allylic strain.11. The compound of claim 6 , wherein monomers or oligomers of Formula I comprise substitutions having varying degrees of flexibility imparted by monomers comprising the ...

Stereoselective synthesis of perhydro-3,6-dialkyl-2-benzo[b]furanones and analogs

Synthetic methods of preparing perhydro-3,6-dimethyl-2-benzo[b]furanones, in particular dihydromintlactone, and analogs through reaction of dehydrogenation of menthanediols and analogs with a base in the presence of (carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II) as catalyst in good stereoselectivity and yields under stereochemistry controlled conditions are disclosed.

Production method for pyrazole-amide compound

or a pharmaceutically acceptable salt thereof, or a hydrate thereof.

ASYMMETRIC AUXILIARY GROUP

To provide a chiral reagent or a salt thereof. 125-. (canceled)27. The oligonucleotide of claim 26 , wherein Gis a hydrogen atom.28. The oligonucleotide of claim 26 , wherein Gis a nitro group.29. The oligonucleotide of claim 26 , wherein Gis a halogen atom.30. The oligonucleotide of claim 26 , wherein Gis a cyano group.31. The oligonucleotide of claim 26 , wherein Gis a group of formula (II).32. The oligonucleotide of claim 26 , wherein Gis a group of formula (III).33. The oligonucleotide of claim 26 , wherein Gis a group of formula (V).34. The oligonucleotide of claim 26 , wherein Gis a nitro group.35. The oligonucleotide of claim 26 , wherein Gis a cyano group.36. The oligonucleotide of claim 26 , wherein Gis a group of formula (III).37. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gto Gare independently Calkyl group claim 26 , Caryl group claim 26 , Caralkyl group claim 26 , Calkyl Caryl group claim 26 , Calkoxy Caryl group claim 26 , or Caryl Calkyl group.38. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gto Gare independently Calkyl group claim 26 , Caryl group claim 26 , Caralkyl group claim 26 , Calkyl Caryl group claim 26 , Calkoxy Caryl group claim 26 , or Caryl Calkyl group.39. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gto Gare independently Calkyl group claim 26 , or Caryl group.40. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gto Gare independently Calkyl group.41. The oligonucleotide of claim 26 , wherein Gis a group of formula (III) claim 26 , wherein Gand Gare Caryl group and Gis Calkyl group.42. The oligonucleotide of claim 26 , wherein Gis a group of formula (V).43. The oligonucleotide of claim 26 , wherein Gis a group of formula (V) claim 26 , wherein each of Gand Gis a hydrogen atom and Gis a 4-methyl group. The present invention is directed to a chiral reagent that ...

Boronic acid derivatives and synthesis thereof

Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the method of use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use as therapeutic agents, for example, β-lactamase inhibitors (BLIs).

C-BULKY P-CHIROGENIC ORGANOPHOSPHORUS COMPOUNDS

In the field of organic phosphorus chemistry, especially the chemistry of bulky organophosphorus compounds, a process for the synthesis of compound of formula (I). This process is especially useful to obtain chiral bulky phosphorus compounds. The present invention also relates to compounds of formula (VII), (VIII), (IX) and (X) and their processes of manufacturing starting from a compound of formula (I). 113-. (canceled)15. The process according to claim 14 , wherein the amine is a mono or a diamine.16. The process according to claim 14 , further comprising heating. The present invention relates to the field of organic phosphorus chemistry, especially the chemistry of bulky organophosphorus compounds. The present invention provides a process for the synthesis of compound of formula (I). This process is especially useful to obtain chiral bulky phosphorus compounds. The present invention also relates to compound of formula (VII), (VIII), (IX) and (X) and their processes of manufacturing starting from a compound of formula (I).The organic phosphorus compounds are currently used in agrochemistry, pharmacy, catalysis, materials, or as flame retardants, extracting agents for hydrometallurgy, or still as chemical reagents. In addition, the properties of organic phosphorus compounds can depend on their chirality.Depending on their substitution, the phosphorus compounds can bear the chirality on the P-center.In recent years the electronically bulky phosphorus ligands (bulky phosphines) bearing substituents such as t-butyl or adamantyl gave a lot of interest in catalysis because they allow the activation of weakly actived substrates. That is explained by the steric hindrance of the ligand, allowing on one hand a weakly coordination of the metal in the catalyst, which makes it more reactive in respect of a substrate, and on the other hand favoring the reductive elimination of the product of the coordination sphere.In the field of chirality, in recent years many chiral ligands ...

Chiral compounds

Optically-active bis(alkynylphosphino) ethane-borane derivative and process for producing the same

An optically-active bis(alkynylphosphino)ethane-borane derivative represented by formula (1): wherein R 1 and R 2 , which may be the same or different, each represent an alkyl group, a phenyl group, an alkylsilyl group or a hydrogen atom; R 3 represents a branched alkyl group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group; and the asterisk * indicates an optically-active site. The derivative (1) is prepared by bromination of, e.g., an (S)-t-butylmethylphosphine-borane, reaction with an alkynyl lithium, deprotonation, followed by oxidative coupling. Deprotection of the derivative (1) by deboranation gives an optically-active bis(alkynylphosphino)ethane derivative useful as a ligand providing an asymmetric catalyst for catalytic asymmetric synthesis. The asymmetric catalyst having the ligand exhibits high selectivity and catalyst activity.

Preparation of Partially Hydrogenated Rac-Ansa-Metallocene Complexes

The invention relates to a process for preparing hydrogenated or partially hydrogenated, racemic ansa-metallocene complexes by reacting bridged or unbridged transition metal complexes with alkali metal compounds or alkaline earth metal compounds, heating the resulting reaction mixture to a temperature in the range from −78 to 250° C. and at least partially hydrogenating the reaction products in the presence of a suitable catalyst, to the corresponding hydrogenated or partially hydrogenated metallocenes and to their use as catalysts or as a constituent of catalysts for the polymerization of olefinically unsaturated compounds or as reagents or catalysts in stereoselective synthesis.

Preparation of partially hydrogenated rac-ansa-metallocene complexes

The invention relates to a process for preparing hydrogenated or partially hydrogenated, racemic ansa-metallocene complexes by reacting bridged or unbridged transition metal complexes with alkali metal compounds or alkaline earth metal compounds, heating the resulting reaction mixture to a temperature in the range from −78 to 250° C. and at least partially hydrogenating the reaction products in the presence of a suitable catalyst, to the corresponding hydrogenated or partially hydrogenated metallocenes and to their use as catalysts or as a constituent of catalysts for the polymerization of olefinically unsaturated compounds or as reagents or catalysts in stereoselective synthesis.

Chiral connections

Chiral compounds

Chiral compounds of formula (I) are new. M = Ti, Zr, Hf, V, Nb, Ta or a lanthanide element; X = halo, H, 1-10C alkyl, 6-15C aryl, 1-10C alkyl-(6-20C)-aryl, OR<8> or NR<8>R<9>; R<8>, R<9> = 1-10C alkyl, 6-15C aryl, alkylaryl, arylalkyl, fluoroalkyl or fluoroaryl with 1-10C in the alkyl group and 6-20C in the aryl group; R<1>-R<4> = H, 1-10C alkyl, 5-7-membered cycloalkyl optionally substituted by 1-10C alkyl, 6-15C aryl or arylalkyl, or Si(R<10>)3; and 2 adjacent groups may form a 4-15C optionally saturated cyclic group; R<10> = 1-10C alkyl, 3-10C cycloalkyl or 6-15C aryl; R<5> = M<1)<R<11>)R<12>, M<1)<R<11>)(R<12>)-M<1)<R<11>)(R<12>)-, M<1)<R<11>)(R<12>)-C(R<13>)2, C(R<11>)(R<12>), OM<1)<R<11>)(R<12>), C(R<11>)(R<12>)C(R<11>)(R<12>), =BR<11>, =AlR<11>, Ge, Sn, O, S, =SO, =SO2, =NR<11>, =CO, =PR<11> or =P(O)R<11>; R<11>-R<13> = H, halo, 1-10C (fluoro)alkyl, 6-10C (fluoro)aryl, 1-10C alkoxy, 2-10C alkenyl, 7-40C arylalkyl, 8-40C arylalkyl or 7-40C alkylaryl or 2 adjacent groups complete a ring; M<1> = Si, Ge or Sn; A = B, Al, Ga, In, Tl, N, P, As, Sb or Bi; R<6>, R<7> = 1-10C alkyl, 6-15C aryl, 5-7-membered cycloalkyl (optionally substituted by 1-10C alkyl or groups containing heteroatoms), (CR<14>R<15>)mOR<16>, (CR<14>R<15>)mSR<16> or CR<17>R<18>; or R<6>+R<7> = a 4-20C optionally saturated cyclic group, (optionally substituted by 1-10C alkyl, 6-15C aryl, heteroatoms or groups containing heteroatoms); R<14>-R<16> = H, 1-10C alkyl, 3-10C cycloalkyl or 6-15C aryl; R<17>, R<18> = 3-10C cycloalkyl, 6-15C aryl or groups containing heteroatoms; m = 1-4; n = the valency of M minus 2. Also claimed is the enantioselective hydrogenation of imines ...

Chiral compounds

Chirale Verbindungen der allgemeinen Formel I in der die Substituenten folgende Bedeutung haben: M Titan, Zirkonium, Hafnium, Vanadium, Niob, Tantal oder ein Element der Lanthanidenreihe, X Fluor, Chlor, Brom, Iod, Wasserstoff, C 1 - bis C 10 -Alkyl, C 6 - bis C 15 -Aryl, Alkylaryl mit 1 bis 10 C-Atomen im Alkylrest und 6 bis 20 C-Atomen im Arylrest, -OR 8 oder -NR 8 R 9 , wobei R 8 und R 9 C 1 - bis C 10 -Alkyl, C 6 - bis C 15 -Aryl, Alkylaryl, Arylalkyl, Fluoralkyl oder Fluoraryl mit jeweils 1 bis 10 C-Atomen im Alkylrest und 6 bis 20 C-Atomen im Arylrest bedeuten, R 1 bis R 4 Wasserstoff, C 1 - bis C 10 -Alkyl, 5- bis 7-gliedrige Cycloalkyl, das seinerseits ein C 1 - bis C 10 -Alkyl als Substituent tragen kann, C 6 - bis C 15 -Aryl oder Arylalkyl, wobei gegebenenfalls auch zwei benachbarte Reste gemeinsam für 4 bis 15 C-Atome aufweisende gesättigte oder ungesättigte cyclische Gruppen stehen können oder Si(R 10 ) 3 mit R 10 C 1 - bis C 10 -Alkyl, C 3 - bis C 10 -Cycloalkyl oder C 6 - bis C 15 -Aryl, R 5 = BR 11 , = AlR 11 , -Ge-, -Sn-, -O-, -S-, = SO, = SO 2 , = NR 11 , = CO, = PR 11 oder = P(O)R 11 ist, wobei R 11 , R 12 und R 13 gleich oder verschieden sind und ein Wasserstoffatom, ein Halogenatom, eine C 1 -C 10 -Alkylgruppe, eine C 1 -C 10 -Fluoralkylgruppe, eine C 6 -C 10 -Fluorarylgruppe, eine C 6 -C 10 -Arylgruppe, eine C 1 -C 10 -Alkoxygruppe, eine C 2 -C 10 -Alkenylgruppe, eine C 7 -C 40 -Arylalkylgruppe, eine C 8 -C 40 -Arylalkenylgruppe oder eine C 7 -C 40 -Alkylarylgruppe bedeuten oder wobei zwei benachbarte Reste jeweils mit dem sie verbindenden Atomen einen Ring bilden, und M 1 Silicium, Germanium oder Zinn ist, A Bor, Aluminium, Gallium, Indium, Thallium, Stickstoff, Phosphor, Arsen, Antimon oder Wismut R 6 und R 7 verschieden sind und C 1 - bis C 10 -Alkyl, C 6 - bis C 15 -Aryl, Alkylaryl oder Arylalkyl mit jeweils 1 bis 10 C-Atomen im Alkylrest und 6 bis 20 C-Atomen im Arylrest, 5- bis 7-gliedriges Cycloalkyl, das seinerseits mit C 1 - bis C 10 - ...

Optically active chiral diphosphine ligands

An (R) or (S) chiral diphosphine of formula (I): wherein R and R1, which can be identical or different, represent an optionally saturated C 1-10 alkyl group, an optionally saturated C 3-9 cycloalkyl group, a C 5-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C 1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R 4 representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, or R and R1 together represent an optionally saturated C 2-6 substituted alkyl group, an optionally saturated C 3-9 cycloalkyl group, a C 5-10 aryl group, the cycloalkyl or aryl groups being optionally substituted by a C 1-5 alkyl, a halogen, a hydroxy, a C 1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R 4 representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, R2 and R3, which can be identical or different, represent an optionally saturated C 3-8 cycloalkyl group, a C 6-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C 1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R 4 representing an alkyl, an alkoxy or an alkylcarbonyl, the cycloalkyl, aryl groups optionally including one or more heteroatoms, or R2 and R3 together form an optionally saturated C 4-8 cyclic group, a C 6-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C 1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R 4 representing an alkyl, an alkoxy or an alkylcarbonyl, the cyclic and aryl groups optionally including one or more heteroatoms.

Diphosphine ligand and transition metal complex using the same

신규 리간드를 개시한다. 또한 다양한 비대칭 합성 반응에서 우수한 거울상체선택성 및 촉매 효율을 지니는, 특히 높은 촉매 활성을 보이는, 리간드를 이용하여 제조되는 신규 전이 금속 착물을 개시한다. 전이 금속 착물은 리간드로서 하기 화학식으로 표시되는 화합물을 가진다: New ligands are disclosed. Also disclosed are novel transition metal complexes prepared using ligands which exhibit particularly high catalytic activity, with excellent enantioselectivity and catalytic efficiency in various asymmetric synthesis reactions. The transition metal complex has a compound represented by the following formula as ligand: [식 중, R 4 는 수소 원자 또는 치환체를 가질 수 있는 C 1 -6 알킬기이고; R 5 및 R 6 는 독립적으로 치환체를 가질 수 있는 C 1 -6 알킬기이고, 또는 화학식 에서 R 5 및 R 6 는 함께 화학식 로 표시되는 화학식을 형성할 수 있음 [Wherein, R 4 is C 1 -6 alkyl group which may have a hydrogen atom or a substituent; R 5 And R 6 is a C 1 -6 alkyl group which may have a substituent, each independently, or formula R 5 And R 6 together with the formula May form a chemical formula represented by (식 중, 고리 B 는 치환체를 가질 수 있는 3- 내지 8-원 고리임)]. Wherein ring B is a 3- to 8-membered ring which may have substituents.

6,6′-bis-(1-phosphanorbornadiene) diphosphines, their preparation and their uses

A subject of the present invention is new 6,6′-bis-(1-phosphanorbornadiene) diphosphines, their preparation process and their use in asymmetrical catalysis. The new diphosphines correspond to general formula (I): in which R 1 , R 2 , R 3 , R 4 , R 5 are as defined in claim 1.

Catalyst

Chiral compounds of varying conformational rigidity and methods of synthesis

ASYMMETRIC SYNTHESIS.

ESTA INVENCION ES RELATIVA A SINTESIS ASIMETRICA EN LA CUAL UN COMPUESTO PROQUIRICO O QUIRICO ESTA CONECTADO EN LA PRESENCIA DE UN COMPLEJO CATALIZADOR LIGANTE CTIVO PARA PRODUCIR UN PRODUCTO OPTICAMENTE ACTIVO. THIS INVENTION IS RELATIVE TO ASYMMETRICAL SYNTHESIS IN WHICH A PROQUIRIC OR CHIRICAL COMPOUND IS CONNECTED IN THE PRESENCE OF A LIGATING CATALYST COMPLEX TO PRODUCE AN OPTICALLY ACTIVE PRODUCT.

IMIDAZOLIDINONIC ACID SUITES AS REACTION CATALYSTS

Stereoselective ring opening reactions

The present invention relates a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic chiral catalyst to produce a steroisomerically or regioselectively enriched product.

Chiral compounds

Chiral compounds of the formula I ##STR1## where the variables are as described in the specification.

Verfahren zur Darstellung teilweise hydrierter rac-ansa-Metallocen-Komplexe

Die Erfindung betrifft ein Verfahren zur Herstellung von hydrierten oder teilhydrierten, racemischen ansa-Metallocenkomplexen durch Umsetzung von verbrückten oder nichtverbrückten Übergangsmetallkomplexen mit Alkali- oder Erdalkalimetallverbindungen, Erwärmen des so erhaltenen Reaktionsgemisches auf eine Temperatur im Bereich von -78 bis 250 DEG C und zumindest teilweises Hydrieren der Umsetzungsprodukte in Gegenwart eines geeigneten Katalysators, die entsprechenden hydrierten oder teilhydrierten Metallocene sowie deren Verwendung als Katalysatoren oder als Bestandteil von Katalysatoren für die Polymerisation von olefinisch ungesättigten Verbindungen oder als Reagenzien oder Katalysatoren in der stereoselektiven Synthese.

Asymmetric synthesis and catalysis with chiral heterocyclic compounds

This invention relates to chiral heterocyclic compounds useful for asymmetric synthesis and catalysis. More particularly, the invention relates to chiral heterocyclic phosphine, sulfur, and nitrogen compounds for asymmetric synthesis and catalysis in the production of enantiomerically pure products.

Asymmetric synthesis and catalysis with chiral heterocyclic compounds

This invention relates to chiral heterocyclic compounds useful for asymmetric synthesis and catalysis. More particularly, the invention relates to chiral heterocyclic phosphine, sulfur, and nitrogen compounds for asymmetric synthesis and catalysis in the production of enantiomerically pure products.