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Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE ALLYL ALCOHOL COMPOUND
Document Type and Number:
WIPO Patent Application WO/2016/133020
Kind Code:
A1
Abstract:
[Problem] To provide a novel stereoselective method for producing an optically active allyl alcohol compound. [Solution] A method for producing an optically active allyl alcohol compound represented by formula (7) characterized by including a step for reacting a borane reducing agent with a ketone compound represented by formula (5) in the presence of an optically active oxazaborolidine compound. Position-3 stereoisomers generated during the reaction can be removed selectively by acylation by adding an esterifying agent to the product of the above step in the presence of a hydrolase. This method makes it possible to produce optically active allyl alcohol compounds at a high yield and high stereoselectivity, and is useful in industrial practice. (In the formula, R1 and R2 each independently represent an alkyl group having from 1 to 6 carbon atoms, and X represents a halogen atom.)

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Inventors:
FUKUYA SHUNSUKE (JP)
FUJITANI KOJI (JP)
HIDAKA IKUMASA (JP)
Application Number:
PCT/JP2016/054147
Publication Date:
August 25, 2016
Filing Date:
February 12, 2016
Export Citation:
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Assignee:
NISSAN CHEMICAL IND LTD (JP)
International Classes:
C07C29/143; C07C29/74; C07C33/42; C12P7/04; C07B53/00; C07B61/00
Foreign References:
JPS5832834A1983-02-25
JPH0641012A1994-02-15
JP2009185015A2009-08-20
JP2001120297A2001-05-08
JPH09176079A1997-07-08
JPH09255635A1997-09-30
JPS60226870A1985-11-12
Other References:
JYOTHI MADDA ET AL.: "Stereoselective total synthesis of rubrenolide and rubrynolide", TETRAHEDRON : ASYMMETRY, vol. 25, no. Issue 22, 30 November 2014 (2014-11-30), pages 1494 - 1500
E.J COREY ET AL.: "A new system for catalytic enantioselective reduction of achiral ketones to chiral alcohols. Synthesis of chiral a- hydroxy acids", TETRAHEDRON LETTERS, vol. 31, no. 5, 1990, pages 611 - 614, XP002090908, DOI: doi:10.1016/S0040-4039(00)94581-7
Attorney, Agent or Firm:
HANABUSA PATENT & TRADEMARK OFFICE (JP)
A patent business corporation is a なぶさ patent trademark office. (JP)
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