Pd-Catalyzed umpolung asymmetric allylic alkylation of hydrazones to vicinal tertiary and quaternary chiral carbon centers

Abstract

Diastereo- and enantioselective construction of vicinal tertiary and quaternary carbon centers is a great challenge in synthetic chemistry. Herein, we report a facile and efficient protocol to construct vicinal tertiary and quaternary chiral carbon centers in high yields with high regio-, diastereo- and enantioselectivities via Pd-catalyzed umpolung asymmetric allylic alkylation of hydrazones with monosubstituted allyl reagents by using Kündig-type chiral N-heterocyclic carbene as the ligand. The control experiments revealed that the reaction proceeds via the inner-sphere mechanism.