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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (08): 1313-1325. 上一篇    下一篇

综述与进展

手性胺-质子酸催化剂在有机催化不对称合成中的应用

吴秋华a; 高勇军a ;李 芝a ;冯 涛a ;李越敏a
刘伟华a ;张亚斋b; 张会芳c; 王 春*,a
  

  1. (a河北农业大学理学院 保定 071001)
    (b河北承德民族师专化学系 承德 067000)
    (c河北定州冀中职业学院 定州 073000)
  • 收稿日期:2007-08-16 修回日期:2007-11-25 发布日期:2008-08-18
  • 通讯作者: 王 春

Application of Chiral Amine-Protonic Acid Catalysts in Asymmetric Organocatalytic Synthesis

WU, Qiu-Huaa; GAO, Yong-Juna; LI, Zhia; FENG, Taoa ;LI, Yue-Mina ;
LIU, Wei-Huaa ;ZHANG, Ya-Zhaib; ZHANG, Hui-Fangc; WANG, Chun*,a
  

  1. (a College of Science, Agricultural University of Hebei, Baoding 071001)
    (b Department of Chemistry, Chengde Teachers College for Nationalities, Chengde 067000)
    (c Jizhong Vocational College of Dingzhou, Dingzhou 073000)
  • Received:2007-08-16 Revised:2007-11-25 Published:2008-08-18
  • Contact: WANG, Chun

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手性胺-质子酸是近年来发展起来的新型高效、高对映选择性的有机催化体系, 已成功应用于催化不对称Aldol反应、Michael加成反应、Diels-Alder反应和Strecker反应等许多重要的有机合成反应. 价廉易得的质子酸的引入不仅可促进活性中间体烯胺的生成, 并可通过形成的氢键稳定反应的过渡态, 从而显著提高该催化体系的催化活性和立体选择性. 对各类手性胺-质子酸催化剂在有机催化不对称合成反应中的应用、不对称诱导反应的机理、手性胺和质子酸的分子结构对其催化活性和不对称诱导活性的影响进行了评述.

关键词: 不对称有机催化, 手性胺, 质子酸

Chiral amine-protonic acids are highly efficient and excellent enantioselective organocatalysts developed in recent years. They have been successfully applied to a number of enantioselective organic reactions, such as asymmetric aldol condenstion, Michael addition, Diels-Alder cycloaddition, Strecker reaction and so on. The introduction of cheap protonic acids can accelerate the formation of an active enanmine intermediate and stabilize the transition state by hydrogen bonding. Consequently, catalytic activity and enantioselectivity of the catalysis system are remarkably increased. The application of chiral amine-protonic acid catalysts to asymmetric synthesis, the mechanism of asymmetric inducement, and the influence of the structure of chiral amine-protonic acids on the catalytic efficience and enantioselectivity are reviewed in this paper.

Key words: asymmetric organocatalysis, protonic acid, chiral amine