Direct asymmetric aldol reaction in aqueous media using polymer-supported peptide

被引:115
作者
Akagawa, K [1 ]
Sakamoto, S [1 ]
Kudo, K [1 ]
机构
[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan
关键词
peptide catalyst; direct asymmetric aldol reaction; solid support; aqueous conditions; catalyst reuse;
D O I
10.1016/j.tetlet.2005.09.113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PEG-PS resin-supported tripeptide/zinc chloride catalyst system has been developed for use in the direct asymmetric aldol reaction of acetone with aldehydes in aqueous media. The peptide catalyst could be separated from the reaction mixture by filtration, and was reusable at least five times without significant change in its activity and selectivity. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8185 / 8187
页数:3
相关论文
共 43 条
  • [1] Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595
  • [2] Primary amine catalyzed direct asymmetric aldol reaction assisted by water
    Amedjkouh, M
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (08) : 1411 - 1414
  • [3] Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides
    Andreae, MRM
    Davis, AP
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (14) : 2487 - 2492
  • [4] TOWARDS THE CHEMICAL SYNTHESIS OF PROTEINS
    BAYER, E
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (02): : 113 - 129
  • [5] Benaglia M, 2002, ADV SYNTH CATAL, V344, P533, DOI 10.1002/1615-4169(200207)344:5<533::AID-ADSC533>3.0.CO
  • [6] 2-Y
  • [7] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions
    Berkessel, A
    Koch, B
    Lex, J
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1141 - 1146
  • [8] Asymmetric aldol reactions in poly(ethylene glycol) catalyzed by L-proline
    Chandrasekhar, S
    Narsihmulu, C
    Reddy, NR
    Sultana, SS
    [J]. TETRAHEDRON LETTERS, 2004, 45 (23) : 4581 - 4582
  • [9] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
    Cobb, AJA
    Shaw, DM
    Longbottom, DA
    Gold, JB
    Ley, SV
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 84 - 96
  • [10] Direct organocatalytic aldol reactions in buffered aqueous media
    Córdova, A
    Notz, W
    Barbas, CF
    [J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025