Title:
METHOD OF ENANTIOMETRICALLY SELECTIVE NUCLEOPHILIC ADDITION REACTION TO CARBONYL OF ENAMIDE AND METHOD OF SYNTHESIZING OPTICALLY ACTIVE &agr -HYDROXY-&gammad -KETO ACID ESTER AND HYDROXYDIKETONE
Document Type and Number:
WIPO Patent Application WO/2005/070864
Kind Code:
A1
Abstract:
A method of enantiometrically selective nucleophilic addition reaction to carbonyl, which enables asymmetric synthesis of optically active &agr -hydroxy-&gammad -keto acid esters, optically active &agr -hydroxy-&gammad -amino acid esters, hydroxydiketone compounds, etc. being useful as a raw material or synthetic intermediate for the production of pharmaceutical products, agricultural chemicals, perfumes, functional polymers, etc. In this method, the nucleophilic addition reaction of enamide compound accompanied by hydroxyl (-OH) formation to carbonyl is carried out in the presence of a chiral catalyst with copper or nickel.
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Inventors:
KOBAYASHI SHU (JP)
Application Number:
PCT/JP2005/001281
Publication Date:
August 04, 2005
Filing Date:
January 24, 2005
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
KOBAYASHI SHU (JP)
KOBAYASHI SHU (JP)
International Classes:
C07C67/343; C07C269/04; C07D207/18; (IPC1-7): C07C67/343; C07B53/00; C07B61/00; C07C69/738; C07C269/04; C07C271/22; C07D207/18; C07D307/32; C07F7/18
Foreign References:
| JP2003260366A | 2003-09-16 | |||
| JP2003260363A | 2003-09-16 |
Other References:
KOBAYASHI S.: "Catalytic, Asymmetric Mannich-type Reactions of N-Acylimino Esters: Reactivity, Diastereo-and Enantioselectivity, and Application to Synthesis of N-Acylated Amino Acid", J. AM. CHEM. SOC., vol. 125, no. 9, 2003, pages 2507 - 2515, XP002987784
KOBAYASHI S.: "Catalytic, Asymmetric Mannich-type Reactions of N-Acylimino Esters for Direct Formation of N-Acylated Amino Acid Derivatives. Efficient Synthesis of a Novel Inhibitor of Ceramide Trafficking, HPA-12", ORGANIC LETTERS, vol. 4, no. 1, 2002, pages 143 - 145, XP002987199
See also references of EP 1707556A4
J. ORGANIC CHEMISTRY, vol. 63, no. 22, 9 October 1998 (1998-10-09), pages 7764 - 7769
ORGANIC LETTERS, vol. 4, no. 20, 7 September 2002 (2002-09-07), pages 3379 - 3382
KOBAYASHI S.: "Catalytic, Asymmetric Mannich-type Reactions of N-Acylimino Esters for Direct Formation of N-Acylated Amino Acid Derivatives. Efficient Synthesis of a Novel Inhibitor of Ceramide Trafficking, HPA-12", ORGANIC LETTERS, vol. 4, no. 1, 2002, pages 143 - 145, XP002987199
See also references of EP 1707556A4
J. ORGANIC CHEMISTRY, vol. 63, no. 22, 9 October 1998 (1998-10-09), pages 7764 - 7769
ORGANIC LETTERS, vol. 4, no. 20, 7 September 2002 (2002-09-07), pages 3379 - 3382
Attorney, Agent or Firm:
Nishizawa, Toshio (11-1 Minami-Aoyama 6-chom, Minato-ku Tokyo, JP)
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