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化学进展 2009, Vol. 21 Issue (09): 1857-1868 前一篇   后一篇

• 综述与评论 •

有机催化不对称[4+2]环加成反应*

王春**|刘伟华|周欣|李越敏|李云鹏   

  1. (河北农业大学理学院河北省生物无机化学重点实验室   |保定 071001)
  • 收稿日期:2008-09-22 修回日期:2008-11-07 出版日期:2009-09-24 发布日期:2009-09-15
  • 通讯作者: 王春 E-mail:wangc69@yahoo.com.cn
  • 基金资助:

    河北省自然科学基金项目（No. 299158）和河北农业大学非生命学科和新兴学科科研发展基金资助项目.

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Organocatalytic Asymmetric [4+2] Cycloaddition Reactions

Wang Chun**; |Liu Weihua; |Zhou Xin; |Li Yuemin; |Li Yunpeng    

  1. (Hebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, China)
  • Received:2008-09-22 Revised:2008-11-07 Online:2009-09-24 Published:2009-09-15
  • Contact: Wang Chun E-mail:wangc69@yahoo.com.cn

有机催化不对称合成反应是目前国内外研究最为活跃的领域之一。不对称[4+2]环加成（Diels-Alder）反应是合成光学活性环状化合物的有效手段，目前报道的催化不对称Diels-Alder反应的有机催化剂主要有手性咪唑啉酮、手性Br?nsted酸、手性伯胺、金鸡纳碱衍生物等。本文对各类有机催化剂在有机催化不对称Diels-Alder反应中的应用研究进展，以及不对称诱导反应的机理进行了评述。

关键词： 不对称有机催化, 不对称[4 2]环加成反应, 手性化合物

Organocatalytic asymmetric reaction is an increasingly active area in organic synthesis. The asymmetric [4+2] cycloaddition (Diels-Alder) reaction is a versatile tool for the synthesis of a large number of important chiral building blocks and intermediates in the total synthesis of natural products. The reported organocatalysts for asymmetric Diels-Alder reaction include imidazolidinone derivatives, chiral Br?nsted acids, chiral primary amines, cinchona alkaloids, etc. The applications of various organocatalysts in asymmetric Diels-Alder reaction and the asymmetric induction mechanism are reviewed in this paper.

Contents
1 Chiral imidazolidinone derivatives
2 Other chiral secondary amines
3 Chiral primary amines
4 Chiral Br?nsted acids
4.1 TADDOL
4.2 Chiral phosphoric acids
4.3 Other chiral Br?nsted acids
5 Cinchona alkaloid derivatives
6 Others
7 Conclusion

Key words: asymmetric organocatalysis, asymmetric [4 2] cycloaddition reaction, chiral compounds

中图分类号: 

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摘要

有机催化不对称[4+2]环加成反应*