Title:
PROCESS FOR PREPARATION OF OPTICALLY ACTIVE ALLENES
Document Type and Number:
WIPO Patent Application WO/2003/074717
Kind Code:
A1
Abstract:
A process for preparation of optically active allenes represented by the general formula (1): (1) [wherein R2 and R3 are different from each other and each hydrogen, optionally substituted C1−20 alkyl, or optionally substituted C6−20 aryl&semi and R4 is acyl], characterized by reacting in the presence of an enzyme catalyst an allene derivative represented by the general formula (2): (2) [wherein R1 is hydrogen or optionally substituted acyl&semi and R2 and R3 are each as defined above] with an acylating agent having an acyl group represented by R4 when R1s are simultaneously hydrogen or with water when R1s are simultaneously acyl represented by R4. According to this process, optically active allenes can be efficiently prepared from symmetric allene derivatives enantioselectively.
Inventors:
SUZUKI KEISUKE (JP)
MATSUMOTO TAKASHI (JP)
MATSUMOTO TAKASHI (JP)
Application Number:
PCT/JP2002/009085
Publication Date:
September 12, 2003
Filing Date:
September 06, 2002
Export Citation:
Assignee:
JAPAN SCIENCE & TECH CORP (JP)
SUZUKI KEISUKE (JP)
MATSUMOTO TAKASHI (JP)
SUZUKI KEISUKE (JP)
MATSUMOTO TAKASHI (JP)
International Classes:
C07B53/00; C12P7/04; C12P7/62; C12P41/00; (IPC1-7): C12P7/04
Other References:
CLAUDE SPINO: "Synthesis of non-racemic unsymmetrical tetrasubstituted vinylallenes", TETRAHEDRON LETTERS, vol. 41, no. 42, 2000, pages 8033 - 8036, XP004235925
GIUSEPPE GUANTI: "Chemoenzymatic preparation of asymmetrized tris(hydroxymethyl)methane(THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde(BHYMA*) as new highly versatile chiral building blocks", J. ORG. CHEM., vol. 57, no. 5, 1992, pages 1540 - 1554, XP002959860
HAJIME MORI: "Novel diastereoselective allene formation by an ene reaction of significantly twisted 1,3-dienes with singlet oxygen", TETRAHEDRON LETTERS, vol. 40, no. 35, 1999, pages 6461 - 6464, XP004173885
See also references of EP 1482054A4
GIUSEPPE GUANTI: "Chemoenzymatic preparation of asymmetrized tris(hydroxymethyl)methane(THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde(BHYMA*) as new highly versatile chiral building blocks", J. ORG. CHEM., vol. 57, no. 5, 1992, pages 1540 - 1554, XP002959860
HAJIME MORI: "Novel diastereoselective allene formation by an ene reaction of significantly twisted 1,3-dienes with singlet oxygen", TETRAHEDRON LETTERS, vol. 40, no. 35, 1999, pages 6461 - 6464, XP004173885
See also references of EP 1482054A4
Attorney, Agent or Firm:
Kobayashi, Hiroshi (8-7 Yaesu 2-chom, Chuo-ku Tokyo, JP)
Download PDF: