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Progress in Chemistry 2006, Vol. 18 Issue (06): 761-767 Previous Articles   Next Articles

• Review •

Organocatalytic Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones Derived from Carbohydrates

Chun Wang;Yongjun Gao;Yingqun Zhang;Zhi Wang**;Jingjun Ma   

  1. College of Science, Agricultural University of Hebei, Baoding 071001, China
  • Received: Revised: Online: Published:
  • Contact: Zhi Wang
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Chiral ketones derived from carbohydrates are powerful catalysts for organocatalytic asymmetric epoxidation of unfunctionalized olefins. Dioxiranes, which could be generated in situ from chiral ketones and potassium peroxomonosulfate (KHSO5), have been shown to be remarkably promising oxidation reagents for asymmetric epoxidation of cis-olefins, trans-olefins, trisubstituted olefins and terminal olefins. The synthesis method of chiral ketones derived from carbohydrates, the reaction mechanism, the catalytic activity and the asymmetric induction influenced by the structure of chiral ketones and the reaction conditions are reviewed in the paper.
Key words: carbohydrates, chiral ketones, organocatalytic asymmetric epoxidation, unfunctionalized olefins, dioxiranes

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