A Chiral Naphthyridine Diimine Ligand Enables Nickel-Catalyzed Asymmetric Alkylidenecyclopropanations

A novel class of chiral naphthyridine diimine ligands (NDI*) readily accessible fromC(2)-symmetric 2,6-di-(1-arylethyl)anilines is described. The utility of these ligands, particularly one with fluorinated aryl side arms, is demonstrated by a reductive Ni-catalyzed enantioselective alkylidene transfer reaction from 1,1-dichloroalkenes to olefins. This transformation provides direct access to a broad range of synthetically valuable alkylidenecyclopropanes in high yields and enantioselectivities.