Synergistic gold and enamine catalysis: intermolecular alpha-alkylation of aldehydes with allenamides

Aldehydes can be alpha-alkylated with allenamides by the combined action of an organocatalyst and a gold complex. The reaction requires the simultaneous generation of an enamine and a gold-activated allenamide. Importantly, by using a chiral amine as organocatalyst it is possible to obtain aldehyde products featuring all-carbon quaternary stereocenter at their alpha-position, with moderate to good levels of enantioselectivity.