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Progress in Chemistry 2007, Vol. 19 Issue (05): 796-804 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
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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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