Title:
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE COMPOUNDS
Document Type and Number:
WIPO Patent Application WO/2003/074487
Kind Code:
A1
Abstract:
A process for the production of optically active β-hydroxy esters represented by the general formula (&Verbar &Verbar &Verbar ): (&Verbar &Verbar &Verbar ) [wherein R1 is optionally substituted hydrocarbyl or the like; R2 is different from R1 and represents a nitrogenous heterocyclic group represented by the general formula (V) or the like: (V) (wherein the ring may be substituted); R3 is optionally substituted hydrocarbyl or the like; R4 and R5 may be the same or different from each other and are each hydrogen, halogeno, or the like; and * represents an asymmetric center], characterized by reacting a compound represented by the general formula (&Verbar ): (&Verbar ) with a compound represented by the general formula (&Verbar &Verbar ): (&Verbar &Verbar ) [wherein X is halogeno] in the presence of a cinchona alkaloid or the like.
Inventors:
YAMANO TORU (JP)
TAYA NAOHIRO (JP)
OJIDA AKIO (JP)
TAYA NAOHIRO (JP)
OJIDA AKIO (JP)
Application Number:
PCT/JP2003/002563
Publication Date:
September 12, 2003
Filing Date:
March 05, 2003
Export Citation:
Assignee:
TAKEDA CHEMICAL INDUSTRIES LTD (JP)
YAMANO TORU (JP)
TAYA NAOHIRO (JP)
OJIDA AKIO (JP)
YAMANO TORU (JP)
TAYA NAOHIRO (JP)
OJIDA AKIO (JP)
International Classes:
C07D233/64; C07B53/00; C07B61/00; C07D213/55; C07D233/54; (IPC1-7): C07D213/55; C07D233/64
Other References:
OJIDA A. ET AL.: "Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination", ORGANIC LETTERS, vol. 4, no. 18, September 2002 (2002-09-01), pages 3051 - 3054, XP002254690
ANDRES A.M. ET AL.: "Synthesis of chiral alpha,alpha-difluoro-beta-hydroxy esters by enentioselective reformatsky reaction", SYNTHESIS, no. 9, 1996, pages 1070 - 1072, XP002969571
SOAI K., OSHIO A., SAITO T.: "Enantioselective reformatsky reaction with ketones. Asymmetric synthesis of beta-(tert-hydroxy) esters", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 9, 1993, pages 811 - 812, XP002969572
PINI D., MASTANTUONO A., SALVADORI P.: "New chiral ligand for optically active beta-hydroxy esters synthesis by enantioselective reformatsky reactions", TETRAHEDRON: ASYMMETRY, vol. 5, no. 10, 1994, pages 1875 - 1876, XP002969573
ANDRES A.M. ET AL.: "Synthesis of chiral alpha,alpha-difluoro-beta-hydroxy esters by enentioselective reformatsky reaction", SYNTHESIS, no. 9, 1996, pages 1070 - 1072, XP002969571
SOAI K., OSHIO A., SAITO T.: "Enantioselective reformatsky reaction with ketones. Asymmetric synthesis of beta-(tert-hydroxy) esters", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 9, 1993, pages 811 - 812, XP002969572
PINI D., MASTANTUONO A., SALVADORI P.: "New chiral ligand for optically active beta-hydroxy esters synthesis by enantioselective reformatsky reactions", TETRAHEDRON: ASYMMETRY, vol. 5, no. 10, 1994, pages 1875 - 1876, XP002969573
Attorney, Agent or Firm:
Takahashi, Shuichi c/o Osaka Plant of Takeda Chemical Industries Ltd. (17-85, Jusohonmachi 2-chome, Yodogawa-k, Osaka-shi Osaka, JP)
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