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化学进展 2007, Vol. 19 Issue (05): 796-804 前一篇   后一篇

• 综述与评论 •

手性联萘酚配合物催化的缺电子烯烃不对称环氧化反应*

高勇军;马晶军;吴秋华;臧晓欢;王春**   

  1. 河北农业大学理学院 保定 071001
  • 收稿日期:2006-06-15 修回日期:2006-08-23 出版日期:2007-05-24 发布日期:2007-05-24
  • 通讯作者: 王春
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Asymmetric Epoxidation of Electron-Deficient Olefins Catalyzed by Coordination Compound Derived From Chiral Binaphthol and Its Derivatives

Gao Yongjun;Ma Jingjun;Wu Qiuhua;Zang Xiaohuan;Wang Chun**   

  1. College of Sciences, Agricultural University of Hebei, Baoding 071001, China
  • Received:2006-06-15 Revised:2006-08-23 Online:2007-05-24 Published:2007-05-24
缺电子烯烃的不对称环氧化反应是有机合成领域最具有挑战性的课题之一。手性联萘酚配体所修饰的催化剂是一种很优异的C2轴对称手性诱导源，可以催化各种α,β－不饱和羰基化合物如α,β－不饱和酮、α,β－不饱和羧酸脂等的不对称环氧化反应，具有良好的催化活性和对映选择性。本文对由手性联萘酚类配体所修饰的小分子催化剂、聚合物负载的催化剂和自负载催化剂在不饱和羰基化合物的催化不对称环氧化反应中的应用进行了综述，探讨了催化剂结构、配位金属原子、添加物、氧化剂、溶剂和反应温度等因素对手性联萘酚催化剂催化效能和对映选择性的影响。
关键词： 手性联萘酚, 不对称环氧化, 对映选择性
The asymmetric epoxidation of electron-deficient olefins,especiallyα,β－unsaturated carbonyl compounds, is one of the most challenging fields in modern organic synthesis in recent years. The catalysts modified by chiral 1,1'-bi-2-naphthol and its derivatives are excellent chiral C2-symmetric inducers which can catalyze the asymmetric epoxidation reaction of electron-deficient olefins with high catalytic activity and excellent enantioselectivity. The substrates involves α,β－unsaturated ketones, α,β－unsaturated carboxylic acid amides, α,β－unsaturated esters and so on. The applications of small molecular catalysts generated from optically active 1,1'-bi-2-naphthol and its derivatives,polymer-supported catalysts and self-supported catalysts in the asymmetric epoxidation reaction of α,β－unsaturated carbonyl compounds are reviewed in this paper. In addition, the catalytic activity and enantioselectivity influenced by the catalysts derived from chiral binaphthol derivatives, cooridinative metal atoms, additives, oxidants, solvents and reaction temperature are also discussed.
Key words: chiral binaphthol, asymmetric epoxidation, enantioselectivity

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