Title:
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE HYDROXYMETHYLATED COMPOUNDS AND CATALYST THEREFOR
Document Type and Number:
WIPO Patent Application WO/2006/080425
Kind Code:
A1
Abstract:
[PROBLEMS] To provide a process for producing optically active hydroxymethylated compounds in high yields at high stereoselectivity with broad substrate generality, and a catalyst for the production. [MEANS FOR SOLVING PROBLEMS] The process comprises reacting a silicon enolate represented by the general formula (1) with formaldehyde in either an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand consisting of a chiral bipyridine or an antipode thereof with Bi(OTf)3: (1) wherein R5 to R7 are each hydrogen, an aliphatic hydrocarbon group, an aliphatic mono- or poly-cyclic hydrocarbon group, a mono- or poly-cyclic aromatic or araliphatic hydrocarbon group, or a heterocyclic group with the proviso that R5 and R7 are different from each other and R6 is not hydrogen; and R8's may be the same or different and are each methyl, ethyl, or isopropyl.
Inventors:
KOBAYASHI SHU (JP)
MANABE KEI (JP)
MANABE KEI (JP)
Application Number:
PCT/JP2006/301293
Publication Date:
August 03, 2006
Filing Date:
January 27, 2006
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
KOBAYASHI SHU (JP)
MANABE KEI (JP)
KOBAYASHI SHU (JP)
MANABE KEI (JP)
International Classes:
C07C45/75; B01J31/22; C07B53/00; C07C49/497; C07C49/513; C07C49/82; C07B61/00
Foreign References:
| JP2001252570A | 2001-09-18 |
Other References:
KOBAYASHI S. ET AL., ORGANIC LETTERS, vol. 7, no. 21, 2005, pages 4729 - 4731, XP003003388
ISHIKAWA S. ET AL., J. AM. CHEM. SOC., vol. 126, no. 39, 2004, pages 12236 - 12237, XP003003389
MANABE K. ET AL.: "Lewis acid-catalyzed asymmetric hydroxymethylation of silicon enolates in aqueous media", TETRAHEDRON, vol. 59, no. 52, 22 December 2003 (2003-12-22), pages 10439 - 10444, XP004479983
See also references of EP 1852412A4
ISHIKAWA S. ET AL., J. AM. CHEM. SOC., vol. 126, no. 39, 2004, pages 12236 - 12237, XP003003389
MANABE K. ET AL.: "Lewis acid-catalyzed asymmetric hydroxymethylation of silicon enolates in aqueous media", TETRAHEDRON, vol. 59, no. 52, 22 December 2003 (2003-12-22), pages 10439 - 10444, XP004479983
See also references of EP 1852412A4
Attorney, Agent or Firm:
Akao, Kenichiro (Kyobashi-Nichiei Biru 3-4 Kyobashi 3-chome, Chuo-k, Tokyo 31, JP)
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