A new stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts

被引:47
作者
Li, GG [1 ]
Wei, HX [1 ]
Willis, S [1 ]
机构
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
关键词
D O I
10.1016/S0040-4039(98)00850-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method has been developed for the stereospecific synthesis of unusual (Z)-beta-branched Baylis-Hillman adducts with high Z/E selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic beta-substituted [alpha-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu2BOTf at -78 degrees C. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4607 / 4610
页数:4
相关论文
共 15 条
  • [1] AGGARWAL V, 1996, J CHEM SOC CHEM COMM, P2713
  • [2] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
    Basavaiah, D
    Rao, PD
    Hyma, RS
    [J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
  • [3] The asymmetric Baylis-Hillman reaction
    Brzezinski, LJ
    Rafel, S
    Leahy, JW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) : 4317 - 4318
  • [4] Ciganek E., 1997, ORG REACTIONS, V51, P201
  • [5] INTRAMOLECULAR BAYLIS-HILLMAN REACTION - A PATHWAY TO SUBSTITUTED COUMARINS
    DREWES, SE
    NJAMELA, OL
    EMSLIE, ND
    RAMESAR, N
    FIELD, JS
    [J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (20) : 2807 - 2815
  • [6] GENISSON Y, 1996, J CHEM SOC P1, P2860
  • [7] LI G, UNPUB SYNLETT
  • [8] Li G-M, UNPUB
  • [9] CHEMISTRY OF SUBSTITUTED (ALPHA-CARBETHOXYVINYL)CUPRATES .2. STEREOSPECIFIC OLEFIN SYNTHESIS
    MARINO, JP
    LINDERMAN, RJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) : 4621 - 4628
  • [10] Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess
    Marko, IE
    Giles, PR
    Hindley, NJ
    [J]. TETRAHEDRON, 1997, 53 (03) : 1015 - 1024