Title:
METHOD OF SYNTHESIZING ASYMMETRIC ALLYLAMINE
Document Type and Number:
WIPO Patent Application WO/2005/051887
Kind Code:
A1
Abstract:
A method of synthesizing an asymmetric allylamine of the following general formula (4), characterized in that an imine of the following general formula (1) is reacted with a tetraallylsilane of the following chemical formula (2) in the presence of a bis-&pgr -allyl palladium complex of the following chemical formula (3) as a catalyst in a solvent containing tetrabutylammonium fluoride. Reaction Formula (1) (In the general formulae, R is selected from the group consisting of o-, m- or p-substituted aromatic, naphthyl, alkenyl, alkyl, furyl, thiophenyl and pyridinyl groups; and R1 is selected from the group consisting of benzyl and aromatic-ring substituted benzyl, allyl and methyl.)
Inventors:
YAMAMOTO YOSHINORI (JP)
FERNANDES RODNEY A (JP)
FERNANDES RODNEY A (JP)
Application Number:
PCT/JP2004/016150
Publication Date:
June 09, 2005
Filing Date:
October 29, 2004
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
YAMAMOTO YOSHINORI (JP)
FERNANDES RODNEY A (JP)
YAMAMOTO YOSHINORI (JP)
FERNANDES RODNEY A (JP)
International Classes:
C07C209/44; C07B61/00; C07C209/52; C07C211/21; (IPC1-7): C07C209/52; C07C211/27; C07C213/00; C07C217/58; C07D213/38; C07D307/52; C07D317/58; C07D333/20
Other References:
NAKAMURA K. ET AL.: "Chiral pi-allypalladium-catalyzed asymmetric allylation of imines: Replacement of allylstannanes by allylsilanes", J. ORG. CHEM., vol. 64, no. 8, 1999, pages 2614 - 2615, XP002983160
FERNANDES R.A. ET AL.: "Chiral bis-pi-allylpalladium complex catalyzed asymmetric allylation of imines: Enhancement of the enantioselectivity and chemical yield in the presence of water", J. AM. CHEM. SOC., vol. 125, no. 46, 19 November 2003 (2003-11-19), pages 14133 - 14139, XP002983161
NAKAMURA H. ET AL.: "Catalytic asymmetric allylation of imines via chiral bis-pi-allylpalladium complexes", J. AM. CHEM. SOC., vol. 120, no. 17, 1998, pages 4242 - 4243, XP002983162
FERNANDES R.A. ET AL.: "Chiral bis-pi-allylpalladium complex catalyzed asymmetric allylation of imines: Enhancement of the enantioselectivity and chemical yield in the presence of water", J. AM. CHEM. SOC., vol. 125, no. 46, 19 November 2003 (2003-11-19), pages 14133 - 14139, XP002983161
NAKAMURA H. ET AL.: "Catalytic asymmetric allylation of imines via chiral bis-pi-allylpalladium complexes", J. AM. CHEM. SOC., vol. 120, no. 17, 1998, pages 4242 - 4243, XP002983162
Attorney, Agent or Firm:
Suzuye, Takehiko c/o Suzuye & Suzuye (7-2 Kasumigaseki 3-chom, Chiyoda-ku Tokyo 13, JP)
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