Sulfonimidamides: Efficient Chiral Iminoiodane Precursors for Diastereoselective Copper-Catalyzed Aziridination of Olefins

Abstract

N-(p-Toluenesulfonyl)-p-toluenesulfonimidamide reacts with iodosylbenzene to afford in situ a chiral iminoiodane. The latter gives, in the presence of a copper(I) catalyst, a nitrene that is very efficiently transferred under stoichiometric conditions to a variety of alkenes with diastereoselectivities up to 60%. [reaction: see text]