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化学进展 2014, Vol. 26 Issue (09): 1492-1505 DOI: 10.7536/PC140319 前一篇   后一篇

• 综述与评论 •

手性催化剂在不对称羰基ene反应中的应用

张永丽, 张瑞, 常宏宏, 魏文珑*, 李兴*   

  1. 太原理工大学 化学化工学院 太原 030024
  • 收稿日期:2014-03-01 修回日期:2014-05-01 出版日期:2014-09-15 发布日期:2014-07-09
  • 通讯作者: 魏文珑, 李兴 E-mail:weiwenlong@tyut.edu.cn;lixing@tyut.edu.cn
  • 基金资助:

    山西省自然科学基金项目（No.2012021007-2，2011011010-2）和山西省高等教育机构科技创新项目基金（No. 20120006）资助

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Asymmetric Carbonyl-ene Reactions Promoted by Chiral Catalysts

Zhang Yongli, Zhang Rui, Chang Honghong, Wei Wenlong*, Li Xing*   

  1. College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China
  • Received:2014-03-01 Revised:2014-05-01 Online:2014-09-15 Published:2014-07-09
  • Supported by:

    The work was supported by the Natural Science Foundation of Shanxi Province (No. 2012021007-2, 2011011010-2), and the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (No. 20120006)

手性高烯丙基醇类化合物是一类非常重要的有机合成中间体，被广泛应用于药物分子和天然产物的合成中，不对称羰基ene反应是构建此类化合物最有效的方法之一，近年来已经取得了巨大进展。目前，在不对称羰基ene反应中的手性催化剂主要有如Mg、Ca、Sc、Ti、Co、Ni、Cu、Rh、Pd、Pt等金属与手性配体络合形成的配合物，以及一些手性有机小分子，大部分都取得了较好的催化活性与对映选择性。本文就此评述了各类手性催化剂在不对称羰基ene反应中的应用，不对称诱导反应的机理，以及催化剂分子结构及反应条件对催化活性和对映选择性的影响。

关键词： 手性高烯丙醇, 羰基ene反应, 不对称催化, 手性有机金属催化剂, 手性有机小分子催化剂

Chiral homoallylic alcohols are important drug intermediates for synthesis of pharmaceutical molecules and nature products. Asymmetric carbonyl-ene reaction is a powerful tool for the preparation of them. The chiral catalysts reported include chiral organometallic complexs and chiral organic molecules, which have achieved good catalytic activity and enantioselectivity. This paper reviews the application of various types of chiral catalysts in asymmetric carbonyl-ene reactions, the reaction mechanism of asymmetric induction, the effect of the structure of the catalysts and reaction conditions on the catalytic activity and enantioselectivity.

Contents
1 Introduction
2 Application of chiral organometallic catalysts in carbonyl-ene reaction
2.1 Chiral alkaline earth metal catalyst
2.2 Chiral transition metal catalyst
2.3 Chiral indium catalyst
3 Chiral organocatalyst
3.1 Chiral phosphorus amide
3.2 Chiral binaphthol and its derivatives
4 Conclusion and outlook

Key words: homoallylic alcohols, carbonyl-ene, asymmetric catalysis, chiral organometallic catalysts, chiral organic molecular catalysts

中图分类号: 

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