Title:
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE &agr -HYDROXYPHOSPHONIC ACIDS AND DERIVATIVES THEREOF, OPTICALLY ACTIVE ALUMINUM(SALALEN) COMPLEXES AND PROCESS FOR PRODUCTION OF THE COMPLEXES, AND PROCESS FOR PRODUCTION OF SALALEN LIGANDS
Document Type and Number:
WIPO Patent Application WO/2006/109442
Kind Code:
A1
Abstract:
A process by which not only aromatic aldehydes but also aliphatic aldehydes can be converted into optically active &agr -hydroxyphosphonic acids or derivatives thereof with sufficiently high enantioselectivity, more specifically, a process for the production of optically active &agr -hydroxyphosphonic acids or derivatives thereof, characterized by conducting asymmetric hydrophosphonylation of an aldehyde with phosphonic acid or a derivative thereof by the use of a catalyst consisting of an optically active aluminum(salalen) complex represented by the general formula (I), (I'), (II) or (II'): wherein R1's are each independently alkyl or aryl; R2's are each independently alkyl or aryl; R3's are each independently alkyl or aryl, or two R3's may be united to form a ring; R4's are each independently hydrogen, halogeno, alkyl, alkoxy, nitro, or cyano; R5 is alkyl; and X1 is halogeno, alkyl, alkoxy, acetoxy, or toluenesulfonyloxy.
Inventors:
KATSUKI TSUTOMU (JP)
SAITO BUNNAI (JP)
SAITO BUNNAI (JP)
Application Number:
PCT/JP2006/305539
Publication Date:
October 19, 2006
Filing Date:
March 20, 2006
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
KATSUKI TSUTOMU (JP)
SAITO BUNNAI (JP)
KATSUKI TSUTOMU (JP)
SAITO BUNNAI (JP)
International Classes:
C07F9/40; B01J31/22; C07C249/02; C07C251/24; C07F5/06; C07B53/00; C07B61/00
Foreign References:
| JPS4621933B1 | ||||
| JPH08319258A | 1996-12-03 | |||
| JP2003183252A | 2003-07-03 | |||
| JP2002513734A | 2002-05-14 |
Other References:
YEORI A. ET AL.: "Salalen: a hybrid Salan/Salen tetradentate [ONNO]-type ligand and its coordination behavior with group IV metals", INORG. CHEM. COMMUN., vol. 7, 2004, pages 280 - 282, XP003000296
SAITO B. ET AL.: "Synthesis of an Optically Active C1-Symmetric Al(salalen) Complex and Its Application to the Catalytic Hydrophosphorylation of Aldehydes", ANGEW. CHEM. INT. ED., vol. 44, 18 July 2005 (2005-07-18), pages 4600 - 4602, XP003000297
See also references of EP 1873160A4
A. YEORI; S. GENDLER; S. GROYSMAN; I. GOLDBERG; M. KOL, JNORG. CHEM. COMMUN., 28 July 2004 (2004-07-28), pages 0 - 282
T. ARAI; M. BOUGAUCHI; H. SASAI; M. SHIBASAKI, J. ORG. CHEM., vol. 61, 1996, pages 2926 - 2927
H. SASAI; M. BOUGAUCHI; T. ARAI; M. SHIBASAKI, TETRAHEDRON LETT., vol. 38, 1997, pages 2717 - 2720
J. P. DUXBURY; A. CAWLEY; M. THORNTON-PETT; L. WANTZ; J. N. D. WARNE; R. GREATREX; D. BROWN; T. P. KEE, TETRAHEDRON LETT., vol. 40, 1999, pages 4403 - 4406
C.V. WARD; M. JIANG; T.P. KEE, TETRAHEDRON LETT., vol. 41, 2000, pages 6181 - 6184
J. P. DUXBURY; J. N. D. WARNE; R. MUSHTAQ; C. WARD; M. THORNTON-PETT; M. JIANG; R. GREATREX; T. P. KEE, ORGANOMETALLICS, vol. 19, 2000, pages 4445 - 4457
T. P KEE; T. D. NIXON, TOPICS IN CURRENT CHEMISTRY, vol. 223, 2003, pages 45 - 65
SAITO B. ET AL.: "Synthesis of an Optically Active C1-Symmetric Al(salalen) Complex and Its Application to the Catalytic Hydrophosphorylation of Aldehydes", ANGEW. CHEM. INT. ED., vol. 44, 18 July 2005 (2005-07-18), pages 4600 - 4602, XP003000297
See also references of EP 1873160A4
A. YEORI; S. GENDLER; S. GROYSMAN; I. GOLDBERG; M. KOL, JNORG. CHEM. COMMUN., 28 July 2004 (2004-07-28), pages 0 - 282
T. ARAI; M. BOUGAUCHI; H. SASAI; M. SHIBASAKI, J. ORG. CHEM., vol. 61, 1996, pages 2926 - 2927
H. SASAI; M. BOUGAUCHI; T. ARAI; M. SHIBASAKI, TETRAHEDRON LETT., vol. 38, 1997, pages 2717 - 2720
J. P. DUXBURY; A. CAWLEY; M. THORNTON-PETT; L. WANTZ; J. N. D. WARNE; R. GREATREX; D. BROWN; T. P. KEE, TETRAHEDRON LETT., vol. 40, 1999, pages 4403 - 4406
C.V. WARD; M. JIANG; T.P. KEE, TETRAHEDRON LETT., vol. 41, 2000, pages 6181 - 6184
J. P. DUXBURY; J. N. D. WARNE; R. MUSHTAQ; C. WARD; M. THORNTON-PETT; M. JIANG; R. GREATREX; T. P. KEE, ORGANOMETALLICS, vol. 19, 2000, pages 4445 - 4457
T. P KEE; T. D. NIXON, TOPICS IN CURRENT CHEMISTRY, vol. 223, 2003, pages 45 - 65
Attorney, Agent or Firm:
Sugimura, Kosaku (2-4 Kasumigaseki 3-chom, Chiyoda-ku Tokyo 13, JP)
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