Asymmetric organocatalytic epoxidations: reactions, scope, mechanisms, and applications

Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7406-26. doi: 10.1002/anie.201400241. Epub 2014 Jun 11.

Abstract

Chiral epoxides serve as versatile building blocks in the synthesis of complex organic frameworks. The high strain imposed by the three-membered ring system makes epoxides prone to a variety of nucleophilic ring-opening reactions. Since the development of the Sharpless epoxidation, there have been many important contributions and advances in this area. With the rapid development of the field of asymmetric organocatalysis, a wide range of organocatalysts is now able to catalyze the epoxidation of broad class of unsaturated carbonyl compounds. In this Minireview, recent progress in the development of organocatalytic asymmetric epoxidation methods, the proposed mechanisms of these reactions and their applications as intermediates is reported.

Keywords: epoxidation; organocatalysis; reaction mechanisms; small ring systems; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Catalysis
  • Epoxy Compounds / chemistry*
  • Organic Chemicals / chemistry*

Substances

  • Epoxy Compounds
  • Organic Chemicals