Nickel-Catalyzed Decarboxylative Generation and Asymmetric Allylation of 2-Azaallyl Anions

Abstract

The first nickel-catalyzed asymmetric decarboxylative allylation (DcA) of allyl 2,2-diarylglycinate imines is reported. This transformation utilizes a chiral ferrocenyl bidentate ligand and a Ni(0) precatalyst to mediate the decarboxylative generation and asymmetric allylation of 2-azaallyl anions, affording α-aryl homoallylic imines in modest-to-high yields and moderate-to-high enantiomeric ratios. The resulting Ni-catalyzed transformation proved to be less general in comparison to our previously reported analogous Pd-mediated protocol, but it still exhibited certain advantages in regard to the regio- and enantioselectivity of the C-C bond formation.