A dynamic kinetic esolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3]

被引:111
作者
Akai, S
Tanimoto, K
Kanao, Y
Egi, M
Yanamoto, T
Kita, Y
机构
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
allyl alcohols; asymmetric synthesis; dynamic kinetic resolution; lipases; vanadium;
D O I
10.1002/anie.200503765
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Mix and match: A new type of dynamic kinetic resolution of racemic allyl alcohols uses a combination of lipases and [VO(OSiPh3)3] (1). The 1,3-transposition of allyl alcohols catalyzed by 1 gave thermodynamic mixtures of two regioisomers, which underwent highly enantio-and chemoselective esterification with lipases. Optically enriched allyl acetates were isolated in high yields. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2592 / 2595
页数:4
相关论文
共 48 条
  • [1] Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition:: a concise asymmetric total synthesis of (-)-rosmarinecine
    Akai, S
    Tanimoto, K
    Kanao, Y
    Omura, S
    Kita, Y
    [J]. CHEMICAL COMMUNICATIONS, 2005, (18) : 2369 - 2371
  • [2] AKAT S, 2004, ANGEW CHEM INT EDIT, V43, P1407
  • [3] AKAT S, 2004, ANGEW CHEM, V116, P1431
  • [4] Dynamic kinetic resolution with enzyme and palladium combinations
    Allen, JV
    Williams, JMJ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1859 - 1862
  • [5] [Anonymous], 2003, ANGEW CHEM, V115, P2109
  • [6] Metal oxo complexes as catalysts for the isomerisation of allylic alcohols
    Bellemin-Laponnaz, S
    Le Ny, JP
    [J]. COMPTES RENDUS CHIMIE, 2002, 5 (04) : 217 - 224
  • [7] BORNSCHEUER UT, 1999, HYDROLASES ORGANIC S, P95
  • [8] USE OF OXO-METALLIC DERIVATIVES IN ISOMERIZATION-REACTIONS OF UNSATURATED ALCOHOLS
    CHABARDES, P
    KUNTZ, E
    VARAGNAT, J
    [J]. TETRAHEDRON, 1977, 33 (14) : 1775 - 1783
  • [9] Aminocyclopentadienyl ruthenium complexes as racemization catalysts for dynamic kinetic resolution of secondary alcohols at ambient temperature
    Choi, JH
    Choi, YK
    Kim, YH
    Park, ES
    Kim, EJ
    Kim, MJ
    Park, JW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) : 1972 - 1977
  • [10] Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines
    Choi, YK
    Kim, MJ
    Ahn, Y
    Kim, MJ
    [J]. ORGANIC LETTERS, 2001, 3 (25) : 4099 - 4101