NiH-Catalyzed Remote Asymmetric Hydroalkylation of Alkenes with Racemic -Bromo Amides

Reported here is a terminal-selective, remote asymmetric hydroalkylation of olefins with racemic -bromo amides. The reaction proceeds by NiH-catalyzed alkene isomerization and subsequent alkylation reaction, and can enantioconvergently introduce an unsymmetrical secondary alkyl group from a racemic -bromo amide onto a terminal C(sp(3))-H position along the hydrocarbon chain of the alkene. This mild process affords a range of structurally diverse chiral -alkylalkanoic amides in excellent yields, and high regio- and enantioselectivities. In addition, the synthetic utility of this protocol is further highlighted by the regioconvergent conversion of industrial raw materials of isomeric olefin mixtures into enantioriched -alkylalkanoic amides on large scale.