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1. (WO1992009545) NEW METHODS FOR THE CATALYTIC REDUCTION OF ORGANIC SUBSTRATES
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1992/009545 International Application No.: PCT/US1991/008738
Publication Date: 11.06.1992 International Filing Date: 21.11.1991
Chapter 2 Demand Filed: 19.06.1992
IPC:
C07B 41/02 (2006.01) ,C07B 43/04 (2006.01) ,C07C 29/143 (2006.01) ,C07C 29/147 (2006.01) ,C07C 209/52 (2006.01) ,C07D 207/06 (2006.01) ,C07D 295/023 (2006.01) ,C07D 307/52 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
B
GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
41
Formation or introduction of functional groups containing oxygen
02
of hydroxy or O-metal groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
B
GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
43
Formation or introduction of functional groups containing nitrogen
04
of amino groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
29
Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
132
by reduction of an oxygen-containing functional group
136
of CO containing groups, e.g. -COOH
143
of ketones
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
29
Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
132
by reduction of an oxygen-containing functional group
136
of CO containing groups, e.g. -COOH
147
of carboxylic acids or derivatives thereof
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
209
Preparation of compounds containing amino groups bound to a carbon skeleton
44
by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
52
by reduction of imines or imino-ethers
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
207
Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
02
with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
04
having no double bonds between ring members or between ring members and non-ring members
06
with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
295
Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
02
containing only hydrogen and carbon atoms in addition to the ring hetero elements
023
Preparation; Separation; Stabilisation; Use of additives
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
307
Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
02
not condensed with other rings
34
having two or three double bonds between ring members or between ring members and non-ring members
38
with substituted hydrocarbon radicals attached to ring carbon atoms
52
Radicals substituted by nitrogen atoms not forming part of a nitro radical
Applicants:
MASSACHUSETTS INSTITUTE OF TECHNOLOGY [US/US]; 77 Massachusetts Avenue Cambridge, MA 02139, US
Inventors:
BUCHWALD, Stephen, L.; US
KREUTZER, Kristina, A.; US
WILLOUGHBY, Christopher, A.; US
GROSSMAN, Robert, B.; US
BERK, Scott, C.; US
SPALTENSTEIN, Esther; US
GUTIERREZ, Alberto; US
Agent:
GEARY, William, C., III ; Lahive & Cockfield 60 State Street Boston, MA 02109, US
ENGELLENNER, Thomas, J.; Lahive & Cockfield 60 State Street Boston, MA 02109, US
Priority Data:
616,89221.11.1990US
698,93913.05.1991US
698,94013.05.1991US
749,11123.08.1991US
792,22714.11.1991US
792,22914.11.1991US
792,23314.11.1991US
Title (EN) NEW METHODS FOR THE CATALYTIC REDUCTION OF ORGANIC SUBSTRATES
(FR) NOUVEAU PROCEDE DE REDUCTION CATALYTIQUE DE SUBSTRATS ORGANIQUES
Abstract:
(EN) A process is provided whereby organic carbonyl substrates, including esters, ketones and amides, are reduced in a reaction with a silane reducing reagent and a catalyst. According to the invention esters and ketones can be reduced to alcohols while amides can be reduced to amines, enamines or a mixture thereof. Methods are also provided for catalytically reducing imines to yield amines. Moreover, there is provided a process for the catalytic asymmetric reduction of imines, oximes, hydrazones, and the like, using enantiomerically enriched catalysts, or catalysts in the presence of enantiomerically enriched additives, to provide chiral amine reaction products which are enriched in one enantiomer. Furthermore, there is provided a process for the catalytic asymmetric reduction of ketones, using catalysts in the presence of enantiomerically enriched additives to provide chiral alcohol reaction products which are enriched in one enantiomer.
(FR) Procédé par lequel des substrats de carbonyle organiques, comprenant des esters, des cétones et des amides, sont réduits au cours d'une réaction avec un réactif réducteur de silane et un catalyseur. Selon l'invention, on peut réduire en alcools les esters et les cétones, tandis que les amides peuvent être réduits en amines, en énamines ou en un mélange de ces substances. Des procédés permettent également la réduction catalytique d'imines en amines. On décrit en outre un procédé de réduction catalytique asymétrique d'imines, oximes, hydrazones et analogues, utilisant des catalyseurs enrichis de manière énantiomère, ou des catalyseurs en présence d'additifs enrichis de manière énantiomère, afin d'obtenir des produits de réaction d'amines chiraux qui sont enrichis en un énantiomère. Est également décrit un procédé de réduction catalytique asymétrique de cétones, utilisant des catalyseurs en présence d'additifs enrichis de manière énantiomère, afin d'obtenir des produits de réaction d'alcools chiraux qui sont enrichis en un énantiomère.
Designated States: CA, JP
European Patent Office (AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LU, NL, SE)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
EP0558656JPH06502867CA2096747