Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE α-FLUORO AMINO ACID COMPOUND OR SALT THEREOF
Document Type and Number:
WIPO Patent Application WO/2016/140189
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a novel method for producing an optically active α-fluoro amino acid compound or a salt thereof. More specifically, the purpose is to produce an α-fluoro amino acid compound or a salt thereof, simply and at a high optical purity, using amino acids which are present in large quantities in nature. A method for producing an optically active α-fluoro amino acid compound or a salt thereof, represented by general formula (1): (in the formula, R1, R2, R3, R4 and * are as defined in the description), characterized in that an amino acid compound or salt thereof represented by general formula (2) (in the formula, R1, R2, R3, R4 and * are as defined in the description), and an electrophilic fluorinating agent are reacted in the presence of a metal amide compound.
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Inventors:
KAWABATA TAKEO (JP)
KASAMATSU KOJI (JP)
YOSHIMURA TOMOYUKI (JP)
KASAMATSU KOJI (JP)
YOSHIMURA TOMOYUKI (JP)
Application Number:
PCT/JP2016/056064
Publication Date:
September 09, 2016
Filing Date:
February 29, 2016
Export Citation:
Assignee:
UNIV KYOTO (JP)
International Classes:
C07C269/06; C07C271/22; C07C319/20; C07C323/60; C07B53/00
Domestic Patent References:
| WO2012157504A1 | 2012-11-22 |
Foreign References:
| JP2013028573A | 2013-02-07 |
Other References:
MOHAR,B. ET AL.: "Enantioselective and diastereoselective synthesis of fluorinated dipeptides by late electrophilic fluorination", TETRAHEDRON LETTERS, vol. 46, pages 5029 - 5031, XP025385642, DOI: doi:10.1016/j.tetlet.2005.05.074
HAN,X. ET AL.: "Highly Enantioselective Amination Reactions of Fluorinated Keto Esters Catalyzed by Novel Chiral Guanidines Derived from Cinchona Alkaloids", ADVANCED SYNTHESIS & CATALYSIS, vol. 352, 26 October 2010 (2010-10-26), pages 2778 - 2782
KAWABATA,T. ET AL.: "A Chiral Nonracemic Enolate with Dynamic Axial Chirality: Direct Asymmetric alpha-Methylation of a-Amino Acid Derivatives", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 39, 16 June 2000 (2000-06-16), pages 2155 - 2157
FUJI,K. ET AL.: "Memory of Chirality - A New Principle in Enolate Chemistry", CHEMISTRY A EUROPEAN JOURNAL, vol. 4, no. 3, 10 March 1998 (1998-03-10), pages 373 - 376
KAWABATA,T. ET AL.: "Memory of Chirality: Asymmetric Induction Based on the Dynamic Chirality of Enolates", TOPICS IN STEREOCHEMISTRY, vol. 23, 27 February 2003 (2003-02-27), pages 175 - 205
DAIKI MONGUCHI: "Asymmetric Intramolecular Conjugate Addition of Chiral Enolates via Nonequilibrium", JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 126, 1 August 2006 (2006-08-01), pages 617 - 627
HAN,X. ET AL.: "Highly Enantioselective Amination Reactions of Fluorinated Keto Esters Catalyzed by Novel Chiral Guanidines Derived from Cinchona Alkaloids", ADVANCED SYNTHESIS & CATALYSIS, vol. 352, 26 October 2010 (2010-10-26), pages 2778 - 2782
KAWABATA,T. ET AL.: "A Chiral Nonracemic Enolate with Dynamic Axial Chirality: Direct Asymmetric alpha-Methylation of a-Amino Acid Derivatives", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 39, 16 June 2000 (2000-06-16), pages 2155 - 2157
FUJI,K. ET AL.: "Memory of Chirality - A New Principle in Enolate Chemistry", CHEMISTRY A EUROPEAN JOURNAL, vol. 4, no. 3, 10 March 1998 (1998-03-10), pages 373 - 376
KAWABATA,T. ET AL.: "Memory of Chirality: Asymmetric Induction Based on the Dynamic Chirality of Enolates", TOPICS IN STEREOCHEMISTRY, vol. 23, 27 February 2003 (2003-02-27), pages 175 - 205
DAIKI MONGUCHI: "Asymmetric Intramolecular Conjugate Addition of Chiral Enolates via Nonequilibrium", JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 126, 1 August 2006 (2006-08-01), pages 617 - 627
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
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