Title:
METHOD FOR PRODUCING FIVE-MEMBERED RING-CONTAINING COMPOUND
Document Type and Number:
WIPO Patent Application WO/2012/147925
Kind Code:
A1
Abstract:
Provided is a method for simply producing, by a short step and at a good yield, a stereospecific asymmetric five-membered ring-containing compound that serves as the synthesis intermediate for the formation of a five-membered ring such as a prostaglandin, with stereoselectivity in that diastereoselectivity and enantioselectivity are excellent, but without difficult procedures such as optical resolution. The method for producing a five-membered ring-containing compound involves producing a five-membered ring-containing compound represented by chemical formula (II) by using a cyclization step wherein the α,β-unsaturated nitro compound represented by chemical formula (I) and a 1,4-butadione compound are subjected to condensation and cyclization in a water-insoluble organic solvent and/or oxygen atom-free water-soluble organic solvent in the presence of a catalyst formed from a compound that has a pyrrolidine ring wherein the carbon at the α position of this ring is optically active.
Inventors:
HAYASHI YUJIRO (JP)
Application Number:
PCT/JP2012/061393
Publication Date:
November 01, 2012
Filing Date:
April 27, 2012
Export Citation:
Assignee:
UNIV TOKYO SCIENCE (JP)
ONO PHARMACEUTICAL CO (JP)
HAYASHI YUJIRO (JP)
ONO PHARMACEUTICAL CO (JP)
HAYASHI YUJIRO (JP)
International Classes:
C07C205/18; C07C201/12; C07C205/44; C07D307/42; C07B53/00; C07B61/00
Foreign References:
| JP2009091257A | 2009-04-30 | |||
| US2920081A | 1960-01-05 |
Other References:
HAYASHI, Y. ET AL.: "Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Tandem Michael/Henry Reaction for the Control of Four Stereocenters", ANGEW. CHEM. INT. ED., vol. 46, no. 26, 2007, pages 4922 - 4925, XP055130659
BIN TAN ET AL., ORGANIC LETTERS, vol. 12, 2010, pages 2682 - 2685
H. GOTOH ET AL., ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 45, 2006, pages 6853 - 6856
H. GOTOH ET AL., ORGANIC LETTERS, vol. 9, 2007, pages 2859 - 2862
T. W. GREENE: "Protective Groups in Organic Synthesis", 1999, WILEY
BIN TAN ET AL., ORGANIC LETTERS, vol. 12, 2010, pages 2682 - 2685
H. GOTOH ET AL., ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 45, 2006, pages 6853 - 6856
H. GOTOH ET AL., ORGANIC LETTERS, vol. 9, 2007, pages 2859 - 2862
T. W. GREENE: "Protective Groups in Organic Synthesis", 1999, WILEY
Attorney, Agent or Firm:
KOMIYA, Yoshio et al. (JP)
Yoshio Komiya (JP)
Yoshio Komiya (JP)
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Claims: