Title:
PRODUCTION METHOD FOR OPTICALLY ACTIVE COMPOUND, AND TRIAZOLIUM SALT USED AS CATALYST IN SAME
Document Type and Number:
WIPO Patent Application WO/2017/006929
Kind Code:
A1
Abstract:
The present invention makes it easy to obtain, with good yield and stereoselectivity, an optically active α-tetrasubstituted α-amino nitrile derivative, or an intermediate for the synthesis of said derivative, by reacting a cyanometalate with a compound represented by formula (3), in which R1-R3 are as described, under the presence of a triazolium salt represented by formula (2), in which R5 and R8-R10 are the same or different and represent an aryl group which may be substituted, R6 represents a primary alkyl group which may be substituted, R7 represents a fatty alkyl group which may be substituted, or a cycloalkyl group which may be substituted, and X1 represents a halogen atom or a monovalent anion.
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Inventors:
OOI TAKASHI (JP)
OHMATSU KOHSUKE (JP)
OHMATSU KOHSUKE (JP)
Application Number:
PCT/JP2016/069888
Publication Date:
January 12, 2017
Filing Date:
July 05, 2016
Export Citation:
Assignee:
NAT UNIV CORP NAGOYA UNIV (JP)
International Classes:
C07C303/40; B01J31/02; C07C253/30; C07C255/24; C07C311/19; C07D249/06; C07B53/00; C07B61/00
Foreign References:
| JP2012082155A | 2012-04-26 |
Other References:
OHMATSU, K. ET AL.: "Catalytic asymmetric Mannich- type reactions of a-cyano a-sulfonyl carbanions", CHEMICAL COMMUNICATIONS, vol. 48, no. 64, 2012, pages 7913 - 7915, ISSN: 1359-7345
WANG,H. ET AL.: "Solvent-controlled asymmetric Strecker reaction: stereoselective synthesis of a-trifluoromethylated a-amino acids", ORGANIC LETTERS, vol. 8, no. 7, 2006, pages 1379 - 1381, XP055345311, ISSN: 1523-7060
VACHAL,P. ET AL.: "Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 34, 2002, pages 10012 - 10014, XP002626112, ISSN: 0002-7863
HUANG,X. ET AL.: "Asymmetric Strecker reaction of keto imines catalyzed by a novel chiral bifunctional N,N'-dioxide", ADVANCED SYNTHESIS & CATALYSIS, vol. 348, no. 18, 2006, pages 2579 - 2584, XP055345314, ISSN: 1615-4150
OHMATSU,K. ET AL.: "Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion- Recognition Ability: Application to Asymmetric Alkylation of Oxindoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 5, 2011, pages 1307 - 1309, XP055345317, ISSN: 0002-7863
WANG,H. ET AL.: "Solvent-controlled asymmetric Strecker reaction: stereoselective synthesis of a-trifluoromethylated a-amino acids", ORGANIC LETTERS, vol. 8, no. 7, 2006, pages 1379 - 1381, XP055345311, ISSN: 1523-7060
VACHAL,P. ET AL.: "Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 34, 2002, pages 10012 - 10014, XP002626112, ISSN: 0002-7863
HUANG,X. ET AL.: "Asymmetric Strecker reaction of keto imines catalyzed by a novel chiral bifunctional N,N'-dioxide", ADVANCED SYNTHESIS & CATALYSIS, vol. 348, no. 18, 2006, pages 2579 - 2584, XP055345314, ISSN: 1615-4150
OHMATSU,K. ET AL.: "Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion- Recognition Ability: Application to Asymmetric Alkylation of Oxindoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 5, 2011, pages 1307 - 1309, XP055345317, ISSN: 0002-7863
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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