Ligand Enabled Iridium-Catalyzed Enantioselective Hydroalkenylation of α-Olefins and Styrenes with Acrylamides

A new type of chiral spiro diphosphite ligand has been developed. Using these ligands, iridium-catalyzed highly enantioselective hydroalkenylation of α-olefins and styrenes with acrylamides has been realized. A variety of aliphatic and aromatic alkenes were successfully coupled with acrylamides to produce γ-substituted chiral acrylamides. The reaction exhibits excellent branched selectivity and high enantioselectivity along with broad substrate scope and good functional group tolerance. DFT calculations indicate that the methyl groups in the ligand play a crucial role in controlling both regioselectivity and enantioselectivity of the reaction.