Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ‑Silylated Allylic Bromides with Benzylzinc Reagents

An enantio- and regioconvergent nickel-catalyzed benzylation of racemic silylated allylic electrophiles with benzylzinc nucleophiles is reported. The key feature of this method is that the homocoupling pathways of both the nucleophile and the electrophile are minimized. A diverse set of electronically modified benzylzinc reagents was tolerated. The vinylsilane products with allylic stereocenters were formed in moderate to high yields with high enantioselectivities. The regioconvergence is the result of the steering effect of the silyl group.