Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND OR SALT THEREOF
Document Type and Number:
WIPO Patent Application WO/2012/105574
Kind Code:
A1
Abstract:
Provided is a production method in which optically active oxazoline is synthesized with fewer production steps using a compound having no optical activity as a starting material compound.
A method for producing an optically active compound represented by formula (3) (wherein * represents an asymmetric carbon atom) or a salt thereof, characterized by cyclizing a compound represented by formula (1) (wherein R1 represents an alkyl group, an alkynyl group, an alkenyl group, an aliphatic heterocyclic group, a cycloalkyl group, an aryl group, an aralkyl group, or an aromatic heterocyclic group, wherein an arbitrary hydrogen atom of such a group may be substituted by a substituent, and R2 represents a hydrogen atom or a group which does not take part in the reaction) in the presence of an asymmetric ligand having one or more coordination sites, a Lewis acid represented by formula (2): MmZn (wherein M represents a metal ion, Z represents a counter anion to M, and m and n represents an integer of 1 to 4), and a sulfonyl halide having an optionally substituted alkyl or phenyl group.
More Like This:
Inventors:
ONOMURA OSAMU (JP)
TSUDA YUTARO (JP)
KURIYAMA MASAMI (JP)
YANAGI TOSHIHARU (JP)
KODAMA KAZUYA (JP)
TSUDA YUTARO (JP)
KURIYAMA MASAMI (JP)
YANAGI TOSHIHARU (JP)
KODAMA KAZUYA (JP)
Application Number:
PCT/JP2012/052176
Publication Date:
August 09, 2012
Filing Date:
January 31, 2012
Export Citation:
Assignee:
UNIV NAGASAKI (JP)
NAGASE CHEMTEX CORP (JP)
ONOMURA OSAMU (JP)
TSUDA YUTARO (JP)
KURIYAMA MASAMI (JP)
YANAGI TOSHIHARU (JP)
KODAMA KAZUYA (JP)
NAGASE CHEMTEX CORP (JP)
ONOMURA OSAMU (JP)
TSUDA YUTARO (JP)
KURIYAMA MASAMI (JP)
YANAGI TOSHIHARU (JP)
KODAMA KAZUYA (JP)
International Classes:
C07D263/14; C07B61/00
Foreign References:
| JP2008290981A | 2008-12-04 | |||
| JP2006219464A | 2006-08-24 | |||
| JP2008037865A | 2008-02-21 |
Other References:
OSAMU ONOMURA ET AL.: "Shokubaiteki Fusai Hitaishokaho ni yoru Kogaku Kassei Oxazoline Gosei", 131ST ANNUAL MEETING OF PHARMACEUTICAL SOCIETY OF JAPAN (SHIZUOKA) HAPPYO YOSHI, vol. VIII-5-1, 1 February 2011 (2011-02-01), XP008169608, Retrieved from the Internet
HONG, M. S. ET AL.: "Enantioselective formation of tert-alkylamines by desymmetrization of 2-substituted serinols", CHEMISTRY--A EUROPEAN JOURNAL, vol. 14, no. 11, 2008, pages 3290 - 3296, XP055077885
See also references of EP 2671877A4
G. JONES; C. J. RICHARDS, TETRAHEDRON LETTERS, vol. 42, 2001, pages 5553 - 5555
A. L. BRAGA ET AL., TETRAHEDRON ASYMMETRY, vol. 14, 2003, pages 3291 - 3295
DANIEL OBRECHT ET AL., J. ORG. CHEM., vol. 61, 1996, pages 4080 - 4086
J. AM. CHEM. SOC., vol. 113, 1991, pages 728 - 729
HONG, M. S. ET AL.: "Enantioselective formation of tert-alkylamines by desymmetrization of 2-substituted serinols", CHEMISTRY--A EUROPEAN JOURNAL, vol. 14, no. 11, 2008, pages 3290 - 3296, XP055077885
See also references of EP 2671877A4
G. JONES; C. J. RICHARDS, TETRAHEDRON LETTERS, vol. 42, 2001, pages 5553 - 5555
A. L. BRAGA ET AL., TETRAHEDRON ASYMMETRY, vol. 14, 2003, pages 3291 - 3295
DANIEL OBRECHT ET AL., J. ORG. CHEM., vol. 61, 1996, pages 4080 - 4086
J. AM. CHEM. SOC., vol. 113, 1991, pages 728 - 729
Attorney, Agent or Firm:
IWATANI, Ryo (JP)
Tatsu Iwatani (JP)
Tatsu Iwatani (JP)
Download PDF:
Claims: