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

Article abstract of DOI:10.1016/S0040-4020(98)00519-5

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.