Copper-Catalyzed Asymmetric Aminocyanation of Arylcyclopropanes for Synthesis of γ-Amino Nitriles

Abstract

A facile approach for the synthesis of enantiopure γ-amino nitriles by copper-catalyzed aminocyanation of arylcyclopropanes is disclosed, which undergoes the highly enantioselective ring-opening reaction of cyclopropanes. The strategy utilizes N-fluorobenzenesulfonimide as nucleophilic nitrogen source as well as oxidant and trimethylsilyl cyanide as the other nucleophile, and it probably operates via a key radical cation intermediate. This reaction provides an efficient platform for asymmetric 1,3-difunctionalization of cyclopropanes.