Copper-Catalyzed Rearrangement of N-Aryl Nitrones into Epoxyketimines

摘要

α,β-Epoxyaldimines are densely functionalized intermediates that combine the reactivity of an epoxide with the electro-philicity of an aldimine within a three-carbon fragment. Accordingly, these compounds have been shown to be valuable precursors for the diastereoselective preparation of epoxy-substituted β-lactams, α-hydroxyaziridines, amino alcohols, oxazolidinones, and phytosphingosine lipid backbones (Scheme 1). α,β-Epoxyaldimines are usually pre- pared by condensation of the corresponding epoxyaldehyde with an amine. Unfortunately, corresponding methods for the preparation of α,β-epoxyketimines are sparse and few alternative methods have been reported. Development of a simple and general method for the preparation of α,β-epoxyketimines would facilitate the exploration of the analogous reactivity of these highly substituted and densely functionalized intermediates.