Nickel-Catalyzed Enantioselective C(sp³)–C(sp³) Cross-Electrophile Coupling of <i>N</i>-Sulfonyl Styrenyl Aziridines with Alkyl Bromides

Abstract

Herein, we report the first example of a highly enantioselective alkylative aziridine ring opening. Under the catalysis of a chiral nickel/pyridine-imidazoline complex, asymmetric C(sp³)-C(sp³) cross-electrophile coupling between racemic <i>N</i>-sulfonyl styrenyl aziridines and readily available primary alkyl bromides furnishes a variety of highly enantioenriched phenethylamine derivatives with complete regiocontrol and good functional group tolerance. Preliminary mechanistic studies support a reaction pathway consisting of regioselective iodolysis of aziridines <i>in situ</i> and subsequent enantioconvergent coupling of the generated β-amino benzyl iodides with alkyl bromides.