WO2009068284A3 - Process for the stereoselective reduction of ketoimines catalysed by trichlorosilane - Google Patents

Process for the stereoselective reduction of ketoimines catalysed by trichlorosilane Download PDF

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Publication number
WO2009068284A3
WO2009068284A3 PCT/EP2008/010079 EP2008010079W WO2009068284A3 WO 2009068284 A3 WO2009068284 A3 WO 2009068284A3 EP 2008010079 W EP2008010079 W EP 2008010079W WO 2009068284 A3 WO2009068284 A3 WO 2009068284A3
Authority
WO
WIPO (PCT)
Prior art keywords
ketoimines
trichlorosilane
catalysed
stereoselective reduction
stereoselective
Prior art date
Application number
PCT/EP2008/010079
Other languages
French (fr)
Other versions
WO2009068284A2 (en
Inventor
Maurizio Benaglia
Stefania Guizzetti
Original Assignee
Universita Degli Studi Di Milano
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP07023240A external-priority patent/EP2065371A1/en
Priority claimed from EP08016622A external-priority patent/EP2166002A1/en
Application filed by Universita Degli Studi Di Milano filed Critical Universita Degli Studi Di Milano
Publication of WO2009068284A2 publication Critical patent/WO2009068284A2/en
Publication of WO2009068284A3 publication Critical patent/WO2009068284A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton 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
    • C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton 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 by reduction of imines or imino-ethers

Abstract

The invention relates to a process for the preparation of enantiomerically enriched amines from ketoimines with trichlorosilane in the presence of picolinic acid derivatives of general formula (I) wherein R1-R7 are as defined in the description as catalysts.
PCT/EP2008/010079 2007-11-30 2008-11-27 Process for the stereoselective reduction of ketoimines catalysed by trichlorosilane WO2009068284A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP07023240A EP2065371A1 (en) 2007-11-30 2007-11-30 Chiral organic catalysts for the stereoselective reduction of carbon-nitrogen double bonds for the preparation of enantiomerically enriched amines
EP07023240.0 2007-11-30
EP08016622.6 2008-09-22
EP08016622A EP2166002A1 (en) 2008-09-22 2008-09-22 Chiral organic catalysts for the enantioselective reduction of n-alkyl and n-benzyl-substituted alicyclic and cyclic imines

Publications (2)

Publication Number Publication Date
WO2009068284A2 WO2009068284A2 (en) 2009-06-04
WO2009068284A3 true WO2009068284A3 (en) 2009-12-17

Family

ID=40679042

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/010079 WO2009068284A2 (en) 2007-11-30 2008-11-27 Process for the stereoselective reduction of ketoimines catalysed by trichlorosilane

Country Status (1)

Country Link
WO (1) WO2009068284A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012201962A1 (en) 2011-10-13 2013-04-18 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Substituted amino alcohols as chiral dopants

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0256982A2 (en) * 1986-08-04 1988-02-24 Ciba-Geigy Ag Method for the preparation of optically active secondary aryl amines
WO2007101769A1 (en) * 2006-03-09 2007-09-13 Evonik Degussa Gmbh Process for the hydrogenation of imines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0256982A2 (en) * 1986-08-04 1988-02-24 Ciba-Geigy Ag Method for the preparation of optically active secondary aryl amines
WO2007101769A1 (en) * 2006-03-09 2007-09-13 Evonik Degussa Gmbh Process for the hydrogenation of imines

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ANDREI V. MALKOV ET AL.: "Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 45, 2006, DEVCH VERLAG, WEINHEIM., pages 1432 - 1435, XP002480581 *
DONG PEI ET AL.: "S-Chiral sulfinamides as highly enantioselective organocatalysts", ORGANIC LETTERS, vol. 8, no. 25, 2006, USAMERICAN CHEMICAL SOCIETY, pages 5913 - 5915, XP002480582 *
IWASAKI F ET AL: "First chemo- and stereoselective reduction of imines using trichlorosilane activated with N-formylpyrrolidine derivatives", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 42, no. 13, 26 March 2001 (2001-03-26), pages 2525 - 2527, XP004232288, ISSN: 0040-4039 *
ONOMURA ET AL: "New organic activators for the enantioselective reduction of aromatic imines with trichlorosilane", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 47, no. 22, 29 May 2006 (2006-05-29), pages 3751 - 3754, XP005407348, ISSN: 0040-4039 *
ZHENG ET AL: "Enantioselective hydrosilylation of ketimines with trichlorosilane promoted by chiral N-picolinoylaminoalcohols", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 48, no. 45, 10 October 2007 (2007-10-10), pages 7934 - 7937, XP022293809, ISSN: 0040-4039 *

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Publication number Publication date
WO2009068284A2 (en) 2009-06-04

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