Title:
PROCESS FOR THE ALLYLATION OF N-ACYLHYDRAZONES
Document Type and Number:
WIPO Patent Application WO/2005/082840
Kind Code:
A1
Abstract:
[PROBLEMS] To provide a novel process for the allylation of N-acylhydrazones by which enantioselectively allylated N-acylhydrazines can be efficiently obtained. [MEANS FOR SOLVING PROBLEMS] A process for the production of enantioselectively allylated N-acylhydrazines represented by the general formula [3]: [3] [wherein R0 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, or -COOR1 (wherein R1 is a hydrocarbon group); R2 is acyl; R3 and R4 are each hydrogen, or one of R3 and R4 is hydrogen and the other is a hydrocarbon group; and R5 and R6 are each independently hydrogen or a hydrocarbon group], characterized by reacting an N-acylhydrazone represented by the general formula [1]: [1] [wherein R0 and R2 are as defined above] with an allylating agent such as allyltrichlorosilane or crotyltrichlorosilane in the presence of a chiral phosphine oxide.
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Inventors:
KOBAYASHI SHU (JP)
SUGIURA MASAHARU (JP)
SUGIURA MASAHARU (JP)
Application Number:
PCT/JP2005/002981
Publication Date:
September 09, 2005
Filing Date:
February 24, 2005
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
KOBAYASHI SHU (JP)
SUGIURA MASAHARU (JP)
KOBAYASHI SHU (JP)
SUGIURA MASAHARU (JP)
International Classes:
C07C227/04; C07C227/18; C07C229/08; C07C241/02; C07C243/38; C07B61/00; (IPC1-7): C07C241/02; C07C227/04; C07C227/18; C07C229/08; C07C243/38
Other References:
OGAWA C. ET AL: "Chusei Haiigata Yiki Shokubai o Mochiiru Koritsuteki alpha-Amino Acid Goseiho no Kaihatsu.", THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU., vol. 84, no. 2, 11 March 2004 (2004-03-11), pages 1270, XP002991806
FERRARIS D. ET AL: "Catalytic, Enantioselective Alkylations of N,O-Acetals.", J.ORG.CHEM., vol. 64, 1999, pages 2168 - 2169, XP002991807
HAMADA T. ET AL: "Catalytic Asymetric Allylation of Hydrazono Esters in Aqueous Media by Using ZnF2-Chiral Diamine.", ANGEW.CHEM.INT.ED., vol. 42, 2003, pages 3927 - 3930, XP002991808
See also references of EP 1721890A4
FERRARIS D. ET AL: "Catalytic, Enantioselective Alkylations of N,O-Acetals.", J.ORG.CHEM., vol. 64, 1999, pages 2168 - 2169, XP002991807
HAMADA T. ET AL: "Catalytic Asymetric Allylation of Hydrazono Esters in Aqueous Media by Using ZnF2-Chiral Diamine.", ANGEW.CHEM.INT.ED., vol. 42, 2003, pages 3927 - 3930, XP002991808
See also references of EP 1721890A4
Attorney, Agent or Firm:
Saeki, Norio (Aminosan Kaikan Building 15-8, Nihonbashi 3-chom, Chuo-ku Tokyo 27, JP)
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