Direct Chemical Method for Preparing 2,3-Epoxyamides Using Sodium Chlorite

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.