Concerted catalytic reactions for conversion of ketones or enol acetates to chiral acetates

被引:54
作者
Jung, HM
Koh, JH
Kim, MJ
Park, J
机构
[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea
[2] Pohang Univ Sci & Technol, Div Mol & Life Sci, Pohang 790784, South Korea
关键词
D O I
10.1021/ol9914043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Enol acetates or ketones asymmetrically transformed to chiral acetates in high yields with high optical purities through multistep reactions catalyzed by a lipase and a ruthenium complex. 2,6-Dimethylheptan-4-ol was chosen as a suitable hydrogen donor, and 4-chlorophenyl acetate was used as an acyl donor for the conversion of ketones.
引用
收藏
页码:409 / 411
页数:3
相关论文
共 40 条
  • [1] THE OXIDATION POTENTIALS OF ALDEHYDES AND KETONES
    ADKINS, H
    ELOFSON, RM
    ROSSOW, AG
    ROBINSON, CC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (11) : 3622 - 3629
  • [2] Dynamic kinetic resolution with enzyme and palladium combinations
    Allen, JV
    Williams, JMJ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1859 - 1862
  • [3] Ruthenium(II)-catalyzed Oppenauer-type oxidation of secondary alcohols
    Almeida, MLS
    Beller, M
    Wang, GZ
    Backvall, JE
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) : 1533 - 1536
  • [4] (CYCLOPENTADIENONE)RUTHENIUM CARBONYL-COMPLEXES - A NEW CLASS OF HOMOGENEOUS HYDROGENATION CATALYSTS
    BLUM, Y
    CZARKIE, D
    RAHAMIM, Y
    SHVO, Y
    [J]. ORGANOMETALLICS, 1985, 4 (08) : 1459 - 1461
  • [5] C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS
    BURK, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) : 8518 - 8519
  • [6] Rh-DuPHOS-catalyzed enantioselective hydrogenation of enol esters.: Application to the synthesis of highly enantioenriched α-hydroxy esters and 1,2-diols
    Burk, MJ
    Kalberg, CS
    Pizzano, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4345 - 4353
  • [7] CADDICK S, 1997, ANGEW CHEM, V109, P1221
  • [8] Dynamic kinetic resolution of acyclic allylic acetates using lipase and palladium
    Choi, YK
    Suh, JH
    Lee, D
    Lim, IT
    Jung, JY
    Kim, MJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) : 8423 - 8424
  • [9] MEERWEIN-PONNDORF-VERLEY REDUCTIONS AND OPPENAUER OXIDATIONS - AN INTEGRATED APPROACH
    DEGRAAUW, CF
    PETERS, JA
    VANBEKKUM, H
    HUSKENS, J
    [J]. SYNTHESIS-STUTTGART, 1994, (10): : 1007 - 1017
  • [10] Catalytic racemisation of alcohols: Applications to enzymatic resolution reactions
    Dinh, PM
    Howarth, JA
    Hudnott, AR
    Williams, JMJ
    Harris, W
    [J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7623 - 7626