Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess

被引:153
作者
Marko, IE
Giles, PR
Hindley, NJ
机构
[1] Univ.́ Catholique de Louvain, Département de Chimie, Laboratoire de Chimie Organique, B-1348 Louvain-la-Neuve, Place Louis Pasteur I
关键词
D O I
10.1016/S0040-4020(96)01001-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several chiral amino-alcohols induce asymmetry in the Baylis-Hillman condensation of aldehydes with methyl vinyl ketone. Pressure plays an interesting role in this reaction. A model accounting for the pressure effect and rationalising the observed absolute stereochemistry is discussed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1015 / 1024
页数:10
相关论文
共 34 条
  • [1] ADAM W, 1993, ANGEW CHEM INT EDIT, V32, P1737, DOI 10.1002/anie.199317371
  • [2] RATE ENHANCEMENT EFFECTS IN THE DABCO CATALYZED SYNTHESIS OF HYDROXYALKENOATE ESTERS
    AMEER, F
    DREWES, SE
    FREESE, S
    KAYE, PT
    [J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (05) : 495 - 500
  • [3] STEREOSELECTIVE EPOXIDATION OF HYDROXYENONES - THE SYNTHESIS OF THE SIDE-CHAIN OF CLEROCIDIN
    BAILEY, M
    MARKO, IE
    OLLIS, WD
    RASMUSSEN, PR
    [J]. TETRAHEDRON LETTERS, 1990, 31 (31) : 4509 - 4512
  • [4] ON THE METAL-CATALYZED EPOXIDATION OF ELECTRON-DEFICIENT OLEFINS
    BAILEY, M
    MARKO, IE
    OLLIS, WD
    [J]. TETRAHEDRON LETTERS, 1991, 32 (23) : 2687 - 2690
  • [5] ASYMMETRIC METAL-CATALYZED EPOXIDATION OF ELECTRON-DEFICIENT OLEFINS
    BAILEY, M
    STATON, I
    ASHTON, PR
    MARKO, IE
    OLLIS, WD
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (07) : 495 - 509
  • [6] BAILEY M, 1991, THESIS U SHEFFIELD S
  • [7] CATALYTIC ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-KETONES
    BARRETT, AGM
    KAMIMURA, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (17) : 1755 - 1756
  • [8] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
    Basavaiah, D
    Rao, PD
    Hyma, RS
    [J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
  • [9] BIOCATALYTIC APPROACH TO OPTICALLY-ACTIVE BAYLIS-HILLMAN REACTION-PRODUCTS
    BASAVAIAH, D
    RAO, PD
    [J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (07) : 917 - 923
  • [10] CHIRAL ACRYLATES AS SUBSTRATES IN BAYLIS-HILLMAN REACTION
    BASAVAIAH, D
    GOWRISWARI, VVL
    SARMA, PKS
    RAO, PD
    [J]. TETRAHEDRON LETTERS, 1990, 31 (11) : 1621 - 1624