One-pot synthesis of O-allylhydroxylamines through the organocatalytic oxidation of tertiary allylic amines followed by a [2,3]-meisenheimer rearrangement.

Abstract

A cheap, green, and highly efficient one-pot method for the synthesis of O-protected allylic alcohols is described. By utilizing 2,2,2-trifluoroacetophenone as the organocatalyst and H2 O2 as the oxidant, a variety of allylic amine N-oxides were synthesized, which upon heating are converted to the final products through a [2,3]-Meisenheimer rearrangement.