Copper(I)‐Photocatalyzed Diastereoselective Aziridination of N‐Sulfonyl Imines with Vinyl Azides: Application to Benzo[f][1,2,3]oxathiazepines Dioxides and Fused Isoxazolines

Abstract

AbstractAn in situ generated photoactive copper(I)‐complex‐catalyzed aziridination reaction of cyclic N‐sulfonyl imines with α‐aryl‐substituted vinyl azides irradiated by blue‐LEDs light is reported for the first time. This novel SET process represents a mild, sustainable, and pragmatic method for accessing synthetically resourceful sulfamidate‐fused aziridines in acceptable chemical yields with excellent diastereoselectivities. Delightedly, pharmacologically attractive benzo[f][1,2,3]oxathiazepine dioxides and fused isoxazoline frameworks were achieved through our newly developed metal‐free based ring‐expansion techniques, highlighting the synthetic value of accessed aziridines. Finally, the possible mechanism for [2+1] aza‐cyclization was presented based on the conduction of a series of control experiments.