Title:
METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID
Document Type and Number:
WIPO Patent Application WO/2014/188783
Kind Code:
A1
Abstract:
The purpose of the invention is to provide a production method that makes possible the industrial production of an optically active α-amino acid at high yield and high enantioselectivity, to provide a simple method for producing optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful in the methods for producing the above optically active α-amino acid and α,α-disubstituted α-amino acid. Provided is a method for producing an optically active α-amino acid or salt thereof characterized in that a substituent is introduced at the α carbon of the α-amino acid moiety structure of a metal complex represented by formula (1) by an alkylation reaction, Aldol reaction, Michael reaction, or Mannich reaction, and an optically pure α-amino acid enantiomer or salt thereof is then liberated by decomposing the metal complex by an acid.
Inventors:
MORIWAKI HIROKI (JP)
KAWASHIMA AKI (JP)
TAKEDA RYOSUKE (JP)
KAWAMURA AKIE (JP)
SOLOSHONOK VADIM A (US)
KAWASHIMA AKI (JP)
TAKEDA RYOSUKE (JP)
KAWAMURA AKIE (JP)
SOLOSHONOK VADIM A (US)
Application Number:
PCT/JP2014/058974
Publication Date:
November 27, 2014
Filing Date:
March 27, 2014
Export Citation:
Assignee:
HAMARI CHEMICALS LTD (JP)
International Classes:
C07F15/04; C07C227/32; C07C229/24; C07C229/30; C07C229/36; C07C229/48; C07C231/18; C07C237/06; C07C319/20; C07C323/58; C07D213/55; C07D223/14; C07B53/00
Foreign References:
| JP2011057665A | 2011-03-24 |
Other References:
LUO, X. ET AL.: "Catalytic asymmetric Michael addition of ?,?-unsaturated aldehydes to Ni(II) complexes of the Schiff base of glycine", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, no. 3, 2011, pages 793 - 801, XP055295862
ELLIS,T.K. ET AL.: "Design, Synthesis, and Evaluation of a New Generation of Modular Nucleophilic Glycine Equivalents for the Efficient Synthesis of Sterically Constrained ?-Amino Acids", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 22, 2006, pages 8572 - 8578, XP009108010
SOLOSHONOK,V.A. ET AL.: "Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of ?-substituted pyroglutamic acids", TETRAHEDRON LETTERS, vol. 46, no. 7, 14 February 2005 (2005-02-14), pages 1107 - 1110, XP027862455
ELLIS,T.K. ET AL.: "New generation of nucleophilic glycine equivalents", TETRAHEDRON LETTERS, vol. 46, no. 6, 2005, pages 941 - 944, XP027862412
U. SCHOLLKOPF ET AL., ANGEW. CHEM. INT. ED. ENGL., vol. 20, 1981, pages 798
E. JUARISTI ET AL., J. ORG. CHEM., vol. 60, 1995, pages 6408
R.M. WILLIAMS ET AL., ORG. SYNTH., vol. 80, 2003, pages 31
V.A. SOLOSHONOK ET AL., J. AM. CHEM. SOC., vol. 127, 2005, pages 15296
T. K. ELLIS ET AL., J. ORG. CHEM., vol. 71, 2006, pages 8572 - 8578
N. MAIGROT ET AL., J. ORG. CHEM., vol. 50, 1985, pages 3916 - 3918
ELLIS,T.K. ET AL.: "Design, Synthesis, and Evaluation of a New Generation of Modular Nucleophilic Glycine Equivalents for the Efficient Synthesis of Sterically Constrained ?-Amino Acids", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 22, 2006, pages 8572 - 8578, XP009108010
SOLOSHONOK,V.A. ET AL.: "Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of ?-substituted pyroglutamic acids", TETRAHEDRON LETTERS, vol. 46, no. 7, 14 February 2005 (2005-02-14), pages 1107 - 1110, XP027862455
ELLIS,T.K. ET AL.: "New generation of nucleophilic glycine equivalents", TETRAHEDRON LETTERS, vol. 46, no. 6, 2005, pages 941 - 944, XP027862412
U. SCHOLLKOPF ET AL., ANGEW. CHEM. INT. ED. ENGL., vol. 20, 1981, pages 798
E. JUARISTI ET AL., J. ORG. CHEM., vol. 60, 1995, pages 6408
R.M. WILLIAMS ET AL., ORG. SYNTH., vol. 80, 2003, pages 31
V.A. SOLOSHONOK ET AL., J. AM. CHEM. SOC., vol. 127, 2005, pages 15296
T. K. ELLIS ET AL., J. ORG. CHEM., vol. 71, 2006, pages 8572 - 8578
N. MAIGROT ET AL., J. ORG. CHEM., vol. 50, 1985, pages 3916 - 3918
Attorney, Agent or Firm:
IWATANI, Ryo (JP)
Tatsu Iwatani (JP)
Tatsu Iwatani (JP)
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