Enantioselective Copper-Catalyzed Intermolecular Amino- and Azidocyanation of Alkenes in a Radical Process

Asymmetric copper-catalyzed intermolecular amino- and azidocyanation reactions of alkenes have been developed that proceed via a radical process in which a key benzylic radical intermediate is enantioselectively trapped by a chiral Box/Cu-II cyanide complex. A variety of enantiomerically enriched beta-amino/azido alkylnitriles were efficiently synthesized. The beta-azido alkylnitriles could be converted into a series of highly valuable optically active amine-based building blocks and bioactive compounds.