Enantioselective Direct Vinylogous Allylic Alkylation of 4-Methylquinolones under Iridium Catalysis.

The first enantioselective vinylogous allylic alkylation of 4-methylquinolones has been developed. This iridium-catalyzed reaction introduces an allyl group at the γ-position of 4-methyl-2-quinolones with exclusive branched selectivity and an excellent level of enantioselectivity. This in turn allows for the enantioselective synthesis of γ-allylquinolines and related nitrogenous heterocycles. This is the first application of 4-methylquinolones in an enantioselective transformation.