Synthesis of γ-hydroxy α,β-unsaturated amides by base-induced isomerization of epoxy amides

Abstract

Treatment of 3,4-epoxyamides with LDA affords γ-hydroxy-α,β-unsaturated amides, usually with high ( E)-selectivity. The 3,4-epoxyamides were prepared by the epoxidation of β,γ-unsaturated amides with meta-chloroperbenzoic acid.