Regioselective Transformation of <i>O</i>-Propargylic Arylaldoximes to Four-Membered Cyclic Nitrones by Copper-Catalyzed Skeletal Rearrangement

Abstract

(E)-O-Propargylic arylaldoximes were regioselectively converted, in the presence of copper catalysts, into their corresponding four-membered cyclic nitrones in good to excellent yields. The reactions proceeded via a tandem [2,3]-rearrangement and 4π-electrocyclization of the N-allenylnitrone intermediate and involved cleavage of the carbon-oxygen bond.