Asymmetric epoxidation of chiral allylic alcohols

被引:12
|
作者
Warmerdam, EGJC
vandenNieuwendijk, AMCH
Brussee, J
Kruse, CG
vanderGen, A
机构
[1] LEIDEN UNIV,LEIDEN INST CHEM,GORLAEUS LABS,NL-2300 RA LEIDEN,NETHERLANDS
[2] SOLVAY DUPHAR BV,NL-1380 DA WEESP,NETHERLANDS
关键词
D O I
10.1016/0957-4166(96)00327-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two series of chiral allylic alcohols, derived from alpha,beta-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate system) oxidants were applied. Several three and all theoretically possible erythro epoxides were isolated in enantiomerically and diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2539 / 2550
页数:12
相关论文
共 50 条
  • [1] Asymmetric epoxidation of chiral allylic alcohols
    Tetrahedron Asymmetry, 9 (2539):
  • [2] ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS - THE SHARPLESS EPOXIDATION
    PFENNINGER, A
    SYNTHESIS-STUTTGART, 1986, (02): : 89 - 116
  • [3] Chiral vanadium-based catalysts for asymmetric epoxidation of allylic alcohols
    Murase, N
    Hoshino, Y
    Oishi, M
    Yamamoto, H
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02): : 338 - 339
  • [4] ASYMMETRIC EPOXIDATION OF FLUORINATED ALLYLIC ALCOHOLS
    GOSMINI, C
    DUBUFFET, T
    SAUVETRE, R
    NORMANT, JF
    TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 223 - 230
  • [5] Chiral hydroxamic acids as ligands for the vanadium catalyzed asymmetric epoxidation of allylic alcohols
    Traber, B
    Jung, YG
    Park, TK
    Hong, JI
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2001, 22 (06) : 547 - 548
  • [6] Asymmetric epoxidation of allylic alcohols catalyzed by new chiral vanadium(V) complexes
    Wu, HL
    Uang, BJ
    TETRAHEDRON-ASYMMETRY, 2002, 13 (24) : 2625 - 2628
  • [7] Planar chiral ferrocenes as ligands in the vanadium-catalyzed asymmetric epoxidation of allylic alcohols
    Bolm, C
    Kühn, T
    ISRAEL JOURNAL OF CHEMISTRY, 2001, 41 (04) : 263 - 269
  • [8] Vanadium catalyzed asymmetric epoxidation of allylic alcohols and homoallylic alcohols
    Zhang, Wei
    Yamamoto, Hisashi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [9] Asymmetric syntheses of chiral allylic alcohols
    Schneider, C
    Kazmaier, U
    SYNTHESIS-STUTTGART, 1998, (09): : 1314 - 1320
  • [10] Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides
    Bunge, Alexander
    Hamann, Hans-Juergen
    Dietz, Dennis
    Liebscher, Juergen
    TETRAHEDRON, 2013, 69 (11) : 2446 - 2450