Construction of β-Ketosulfone and α-Amido Ketone Skeletons via Oxaziridine Intermediates

Abstract

Herein, we report a tandem nucleophilic cyclization-thermally triggered rearrangement/cleavage reaction using (E)-β-iodovinyl sulfones and acetohydroxamic acids as readily available substrates. With an oxaziridine serving as the pivotal intermediate, this synthetic protocol allows the temperature-dependent, divergent assembly of α-amido ketone and β-ketosulfone skeletons in an efficient manner. This approach broadens the synthetic utility of high-strain N,O-heterocyclic scaffolds and provides an efficient and versatile synthetic platform for accessing these two valuable functional molecular architectures.