Title:
新規光学活性化合物、カルボン酸誘導体の速度論的光学分割方法およびその触媒
Document Type and Number:
Japanese Patent JP4301004
Kind Code:
B2
Abstract:
The present invention provides a method of kinetic optical resolution of carboxylic acid derivatives using specific optically active catalysts. A racemic or diastereomeric mixture of carboxylic acid derivatives of the formula (A) is reacted with a nucleophile in the presence of an optically active catalyst to form an optically active nucleophile derivative of the formula (B). The catalyst is an optically active compound represented by the formula (C) or (D) Äwherein R<1> is a substituted or unsubstituted, saturated or unsaturated, straight-chain, branched or alicyclic aliphatic hydrocarbon group which can have a heteroatom, R<2> is ethyl or vinyl, and R<5> is hydrogen or methoxy respectivelyÜ.
More Like This:
Inventors:
Hiroshi Ishii
Yasushi Miki
Yoshiro Furukawa
Satoshi Murakami
Yasushi Miki
Yoshiro Furukawa
Satoshi Murakami
Application Number:
JP2003564043A
Publication Date:
July 22, 2009
Filing Date:
January 31, 2003
Export Citation:
Assignee:
Daiso Co., Ltd.
International Classes:
C07D453/04; B01J31/02; C07B57/00; C07C51/083; C07C67/12
Foreign References:
| WO2001074741A1 | ||||
| WO2001000545A1 | ||||
| WO2002010096A1 | ||||
| WO2003011799A1 |
Other References:
SHAH,V.H. et al,Studies on cinchonine derivatives. Part II. Preparation, antimicrobial and anthelmintic activity of N-aryldithiocarbamyl-10,11-H/10,11-dibromo-9- cinchonyl acetate and N-aryl-9-cinchonyloxyacetamides,Journal of the Institution of Chemists(India),1987年,Vol.59, No.6,pp.249-250
ZALIPSKY,S. et al,Attachment of drugs to polyethylene glycols,European Polymer Journal,1983年,Vol.19, No.12,pp.1177-1183
Jianfeng Hang et al.,Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of N-Carboxyanhydrids,J Am Chem Soc,2001年,Vol.123, No.50,pp.12696-12697
von Arx M. et al.,A Ner Reaction Pathway in the Enantioselective Hydrogenation of Activated Ketones on Cinchona-Modified Platinum,J Catal,2001年,Vol.202, No.1,pp.169-176
Torok B et al.,Asymmetric sonochemical reaction Enantioselective hydrogenation of α-ketoesters over platinum catalysts,Ultrasonics Sonochemistry,2000年,Vol.7, No.4,pp.151-155
von Arx M et al.,First Enantioselective Hydrogenation of a Trifluoro-β-ketoester with Cinchona-Modified Platinum,J Catal,2000年,Vol.193, No.1,pp.161-164
Blaser H.U. et al.,Heterogeneous Enantioselective Hydrogenation of Ethyl Pyruvate Catalyzed by Cinchona-Modified Pt Catalysts: Effect of Modifier Structure,J Am Chem Soc,2000年,Vol.122, No.51,pp.12675-12682
Blake A.J. et al.,The Highly enantioselective transformation of silylketenes into α-silylthioesters catalyzed by cinchona alkaloids,Tetrahedron Letters,2001年,Vol.42, No.15,pp.2877-2881
NEFF,D.P. et al,Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives ("naked sugar") as synthetic intermediates. Part XV. New total synthesis of D-threo-L-talo octose,Helvetica Chimica Acta,1991年,Vol.74, No.3,pp.508-516
LOHAY,B.B. et al,Mechanism of osmium-catalyzed asymmetric dihydroxylation (ADH) of alkenes,Tetrahedron Letters,1992年,Vol.33, No.35,pp.5113-5116
Borszeky K et al.,Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids over Cinchonidine Modified Palladium: Nature of Modifier-Reactant Interaction,J Catal,1999年,Vol.187, No.1,pp.160-166
ZALIPSKY,S. et al,Attachment of drugs to polyethylene glycols,European Polymer Journal,1983年,Vol.19, No.12,pp.1177-1183
Jianfeng Hang et al.,Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of N-Carboxyanhydrids,J Am Chem Soc,2001年,Vol.123, No.50,pp.12696-12697
von Arx M. et al.,A Ner Reaction Pathway in the Enantioselective Hydrogenation of Activated Ketones on Cinchona-Modified Platinum,J Catal,2001年,Vol.202, No.1,pp.169-176
Torok B et al.,Asymmetric sonochemical reaction Enantioselective hydrogenation of α-ketoesters over platinum catalysts,Ultrasonics Sonochemistry,2000年,Vol.7, No.4,pp.151-155
von Arx M et al.,First Enantioselective Hydrogenation of a Trifluoro-β-ketoester with Cinchona-Modified Platinum,J Catal,2000年,Vol.193, No.1,pp.161-164
Blaser H.U. et al.,Heterogeneous Enantioselective Hydrogenation of Ethyl Pyruvate Catalyzed by Cinchona-Modified Pt Catalysts: Effect of Modifier Structure,J Am Chem Soc,2000年,Vol.122, No.51,pp.12675-12682
Blake A.J. et al.,The Highly enantioselective transformation of silylketenes into α-silylthioesters catalyzed by cinchona alkaloids,Tetrahedron Letters,2001年,Vol.42, No.15,pp.2877-2881
NEFF,D.P. et al,Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives ("naked sugar") as synthetic intermediates. Part XV. New total synthesis of D-threo-L-talo octose,Helvetica Chimica Acta,1991年,Vol.74, No.3,pp.508-516
LOHAY,B.B. et al,Mechanism of osmium-catalyzed asymmetric dihydroxylation (ADH) of alkenes,Tetrahedron Letters,1992年,Vol.33, No.35,pp.5113-5116
Borszeky K et al.,Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids over Cinchonidine Modified Palladium: Nature of Modifier-Reactant Interaction,J Catal,1999年,Vol.187, No.1,pp.160-166
Attorney, Agent or Firm:
Norihiko Hibi
Einosuke Kishimoto
Akira Watanabe
Einosuke Kishimoto
Akira Watanabe