Aldol reactions on solid phase. Sc(OTf)(3)-catalyzed aldol reactions of polymer-supported silyl enol ethers with aldehydes providing convenient methods for the preparation of 1,3-diol,beta-hydroxy carboxylic acid, and beta-hydroxy aldehyde libraries

被引:48
作者
Kobayashi, S
Hachiya, I
Yasuda, M
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
基金
日本学术振兴会;
关键词
D O I
10.1016/0040-4039(96)01158-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldol reactions on solid phase have been achieved. In the presence of a catalytic amount of scandium triflate (Sc(OTf)(3)), polymer-supported silyl enol ethers reacted with aldehydes to afford the corresponding beta-hydroxy thioester derivatives, which were reduced to I,3-diol and beta-hydroxy aldehyde derivatives, or hydrolyzed to beta-hydroxy carboxylic acid derivatives. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5569 / 5572
页数:4
相关论文
共 18 条
  • [1] BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, V1, P85
  • [2] Colvin E. W., 1981, SILICON ORGANIC SYNT, P165
  • [3] FLEMING I, 1980, CHIMIA, V34, P265
  • [4] Organic chemistry on solid supports
    Fruchtel, JS
    Jung, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01): : 17 - 42
  • [5] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS
    GORDON, EM
    BARRETT, RW
    DOWER, WJ
    FODOR, SPA
    GALLOP, MA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) : 1385 - 1401
  • [6] Solid-phase organic reactions: A review of the recent literature
    Hermkens, PHH
    Ottenheijm, HCJ
    Rees, D
    [J]. TETRAHEDRON, 1996, 52 (13) : 4527 - 4554
  • [7] KOBAYASHI S, 1994, SYNLETT, P689
  • [8] Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library
    Kobayashi, S
    Hachiya, I
    Suzuki, S
    Moriwaki, M
    [J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2809 - 2812
  • [9] SCANDIUM TRIFLUOROMETHANESULFONATE (SC(OTF)3) - A NOVEL REUSABLE CATALYST IN THE DIELS-ALDER REACTION
    KOBAYASHI, S
    HACHIYA, I
    ARAKI, M
    ISHITANI, H
    [J]. TETRAHEDRON LETTERS, 1993, 34 (23) : 3755 - 3758
  • [10] KOBAYASHI S, 1993, SYNLETT, P472