Direct chemical method for preparing 2,3-epoxyamides using sodium chlorite

J Org Chem. 2012 Jul 6;77(13):5515-24. doi: 10.1021/jo300542d. Epub 2012 Jun 12.

Abstract

A direct method for preparing 2,3-epoxyamides from tertiary allylamines via a tandem C-H oxidation/double bond epoxidation using sodium chlorite is reported. Apparently, the reaction course consists of two steps: (i) allylic oxidation of the starting allylamine to corresponding unsaturated allylamide with sodium chlorite followed by (ii) epoxidation of the allylamide to the 2,3-epoxyamide mediated by hypochlorite ion, which is formed in situ by reduction of sodium chlorite. The reaction conditions tolerate the presence of free hydroxyl groups and typical functional groups such as TBS, aryl, alkyl, allyl, acetyl, and benzyl groups; however, when an activated aromatic ring (e.g., sesamol) is present in the substrate, the use of a scavenger is necessary.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylamine / chemistry
  • Chlorides / chemistry*
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Chlorides
  • Epoxy Compounds
  • Allylamine
  • chlorite