Nickel-Catalyzed Enantioselective C(sp)-C(sp) Cross-Electrophile Coupling of -Sulfonyl Styrenyl Aziridines with Alkyl Bromides.

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(sp)-C(sp) cross-electrophile coupling between racemic -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 and subsequent enantioconvergent coupling of the generated β-amino benzyl iodides with alkyl bromides.