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化学进展 2018, Vol. 30 Issue (5): 491-504 DOI: 10.7536/PC171121 前一篇   后一篇

• 综述 •

催化不对称傅-克反应研究进展

张宇, 刘小华, 林丽丽, 冯小明*   

  1. 四川大学化学学院 成都 610064
  • 收稿日期:2017-11-23 修回日期:2018-01-14 出版日期:2018-05-15 发布日期:2018-04-25
  • 通讯作者: 冯小明e-mail:xmfeng@scu.edu.cn E-mail:xmfeng@scu.edu.cn
  • 基金资助:
    国家自然科学基金项目（No.21432006）资助
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Recent Advance in Catalytic Asymmetric Friedel-Crafts Reactions

Yu Zhang, Xiaohua Liu, Lili Lin, Xiaoming Feng*   

  1. College of Chemistry, Sichuan University, Chengdu 610064, China
  • Received:2017-11-23 Revised:2018-01-14 Online:2018-05-15 Published:2018-04-25
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21432006).
催化不对称傅-克反应是构建具有光学活性芳基化合物最有效的方法之一。自从1877年报道了首例傅-克反应后，该反应得到化学家们的关注。最近二十年，许多手性双功能有机小分子催化剂（如金鸡纳碱、手性脯氨醇硅醚、手性磷酸、手性硫脲等）以及金属与手性配体（如手性双氮氧、手性双唑啉、手性席夫碱）形成的配合物催化剂被应用到各类不对称傅-克反应中。本文主要从反应的芳基底物类型分类，对近年来酚、吡咯、呋喃以及噻吩参与的不对称傅-克反应进行简要概述，同时对这类反应所存在的问题和局限性进行总结，并对今后发展方向作了展望。
关键词： 不对称催化, 傅-克反应, 酚, 吡咯, 呋喃
Catalytic asymmetric Friedel-Crafts reaction is one of the most efficient methods for the construction of optically active aryl-or heteroaryl-containing compounds. Since Friedel and Crafts reported the first example in 1877, this reaction has attracted wide attention. In recent twenty years, asymmetric catalytic Friedel-Crafts reaction has been well studied in the presence of a number of chiral bifunctional organocatalysts (such as derivatives of cinchona alkaloids, chiral prolinol ethers, chiral phosphoric acids, chiral thiourea, etc.) and various metal and chiral ligand (chiral N,N'-dioxide, chiral bis(oxazoline), chiral Schiff base) complexes. In this paper, we summarize the recent progress in asymmetric Friedel-Crafts reactions of phenols, pyrroles, furans and thiophenes. Finally, the deficiencies as well as the perspective of the Friedel-Crafts reaction have been highlighted.
Contents
1 Introduction
2 Catalytic asymmetric Friedel-Crafts reactions of phenols
2.1 Imines as the electrophiles
2.2 1, 2-Diketones as the electrophiles
2.3 Nitroalkenes as the electrophiles
2.4 α, β-Unsaturated carbonyl compounds as the electrophiles
2.5 Others double bonds as the electrophiles
3 Catalytic asymmetric Friedel-Crafts reactions of pyrroles
3.1 Nitroalkenes as the electrophiles
3.2 α, β-Unsaturated carbonyl compounds as the electrophiles
3.3 Others
4 Catalytic asymmetric Friedel-Crafts reactions of furans and thiophenes
5 Conclusion
Key words: asymmetric catalysis, Friedel-Crafts reaction, phenols, pyrroles, furans

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催化不对称傅-克反应研究进展