Title:
PROCESS FOR PRODUCING OPTICALLY ACTIVE ESTER
Document Type and Number:
WIPO Patent Application WO/2007/023906
Kind Code:
A1
Abstract:
A process for producing an optically active 2-hydroxybutyric ester (1), characterized by
reacting an optically active 2,3-epoxybutyric ester (2) with a thiol compound in
the presence of scandium trifluoromethanesulfonate or ytterbium trifluoromethanesulfonate to
obtain a compound (3) and subjecting it to a desulfurization reaction. (2) →
(3) → (1) [In the formulae, R represents C1-6 alkyl or C7-8
aralkyl; R1 represents C1-12 alkyl or phenyl; and * indicates
absolute S- or R-configuration.] The process enables an optically active 2-hydroxybutyric
ester having a high optical purity to be obtained in a high yield.
Inventors:
ARAKI TAKAAKI (JP)
YAMAZAKI YUKIYOSHI (JP)
SHIBUYA KIMIYUKI (JP)
YAMAZAKI YUKIYOSHI (JP)
SHIBUYA KIMIYUKI (JP)
Application Number:
PCT/JP2006/316624
Publication Date:
March 01, 2007
Filing Date:
August 24, 2006
Export Citation:
Assignee:
KOWA CO (JP)
ARAKI TAKAAKI (JP)
YAMAZAKI YUKIYOSHI (JP)
SHIBUYA KIMIYUKI (JP)
ARAKI TAKAAKI (JP)
YAMAZAKI YUKIYOSHI (JP)
SHIBUYA KIMIYUKI (JP)
International Classes:
C07C67/317; C07C19/14; C07C69/675; C07C323/52; C07B53/00
Foreign References:
| JPH0436195A | 1992-02-06 |
Other References:
RIEGO J. ET AL.: "Regioselective AlPO4-Al2O3 Promoted Ring-Opening of 2,3-Epoxy Esters", CHEMISTRY LETTERS, no. 9, 1986, pages 1565 - 1568, XP002057815
AGGARWAL V.K. ET AL.: "Highly Enantioselective Darzens Reaction of a Camphor-Derived Sulfonium Amide to Give Glycidic Amides and Their Applications in Synthesis", J. AM. SOC., vol. 124, no. 34, 2002, pages 9964 - 9965, XP002248625
KANG S.-K. ET AL.: "Highly Regioselective Nucleophilic Substitution of Cyclic Carbonates of threo-2,3-Dihydroxy Esters: Synthesis of Optically Pure beta-Hydroxy Esters", J. CHEM. SOC. PERKIN TRANS. I, no. 24, 1994, pages 3513 - 3514, XP002161551
See also references of EP 1918271A4
AGGARWAL V.K. ET AL.: "Highly Enantioselective Darzens Reaction of a Camphor-Derived Sulfonium Amide to Give Glycidic Amides and Their Applications in Synthesis", J. AM. SOC., vol. 124, no. 34, 2002, pages 9964 - 9965, XP002248625
KANG S.-K. ET AL.: "Highly Regioselective Nucleophilic Substitution of Cyclic Carbonates of threo-2,3-Dihydroxy Esters: Synthesis of Optically Pure beta-Hydroxy Esters", J. CHEM. SOC. PERKIN TRANS. I, no. 24, 1994, pages 3513 - 3514, XP002161551
See also references of EP 1918271A4
Attorney, Agent or Firm:
THE PATENT CORPORATE BODY ARUGA PATENT OFFICE (3-6 Nihonbashiningyocho, 1-chom, Chuo-ku Tokyo 13, JP)
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