Title:
METHOD FOR ASYMMETRIC ALLYLATION OF &agr -IMINO ACID
Document Type and Number:
WIPO Patent Application WO/2006/080576
Kind Code:
A1
Abstract:
A method for the asymmetric allylation of an &agr -imino acid, wherein an allylsilane compound is reacted with an an &agr -imino acid having a structure in which an oxycarbonyl group is bonded to a nitrogen atom of the imino group in the presence of a chiral copper catalyst. The above method can be suitably employed for synthesizing an optically active allylglycine analogue by the use of a practical catalytic asymmetric allylation reaction which uses non-expensive raw materials and gives a high reaction yield and high stereoselectivity under mild conditions.
Inventors:
KOBAYASHI SHU (JP)
Application Number:
PCT/JP2006/301920
Publication Date:
August 03, 2006
Filing Date:
January 31, 2006
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
KOBAYASHI SHU (JP)
KOBAYASHI SHU (JP)
International Classes:
C07C269/00; B01J31/22; C07C269/06; C07C271/22; C07B53/00; C07B61/00
Foreign References:
| JP2003260363A | 2003-09-16 | |||
| JP2004099443A | 2004-04-02 |
Other References:
KOBAYASHI S. ET AL.: "Catalytic, Asymmetric Mannich-type Reactions of N-Acylimino Esters: Reactivity, Diastereo- and Enantioselectivity, and Application to Synthesis of N-Acylated Amino Acid Derivatives", J. AM. CHEM., vol. 125, 2003, pages 2507 - 2515, XP002999609
KOBAYASHI S. ET AL.: "Catalytic Asymmetric Synthesis of alpha-Amino Phosphonates Using Enantioselective Carbon-Carbon Bond-Forming Reactions", J. AM. CHEM., vol. 126, no. 21, 2004, pages 6558 - 6559, XP002990307
OLLEVIER T. AND BA T.: "Highly efficient three-component synthesis of protected homoallylic amines by bismuth triflate-catalyzed allylation of aldimines", TETRAHEDRON LETTERS, vol. 44, no. 50, 8 December 2003 (2003-12-08), pages 9003 - 9005, XP004471949
FERRARIS D. ET AL.: "Catalytic, Enantioselective Alkylation of alpha-Imino Esters: The Synthesis of Nonnatural alpha-Amino Acid Derivatives", J. AM. CHEM. SOC., vol. 124, 2002, pages 67 - 77, XP002999610
KOBAYASHI S. ET AL.: "Catalytic Asymmetric Synthesis of alpha-Amino Phosphonates Using Enantioselective Carbon-Carbon Bond-Forming Reactions", J. AM. CHEM., vol. 126, no. 21, 2004, pages 6558 - 6559, XP002990307
OLLEVIER T. AND BA T.: "Highly efficient three-component synthesis of protected homoallylic amines by bismuth triflate-catalyzed allylation of aldimines", TETRAHEDRON LETTERS, vol. 44, no. 50, 8 December 2003 (2003-12-08), pages 9003 - 9005, XP004471949
FERRARIS D. ET AL.: "Catalytic, Enantioselective Alkylation of alpha-Imino Esters: The Synthesis of Nonnatural alpha-Amino Acid Derivatives", J. AM. CHEM. SOC., vol. 124, 2002, pages 67 - 77, XP002999610
Attorney, Agent or Firm:
Nishizawa, Toshio (11-1 Minami-Aoyama 6-chom, Minato-ku Tokyo, JP)
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