Gold(I) operational in synergistic catalysis for the intermolecular α-addition reaction of aldehydes across allenamides

Abstract

Asymmetric organocatalysis is well stablished as a powerful tool to promote chemical transformations with good yields and enantioselectivities. For years, gold(I) has been extensively used for the activation of unsaturated compounds toward different nucleophiles. These two strategies can be combined in a synergistic manner to afford new chemical transformations. Herein we report the synergistic combination of gold(I) catalysis with L-proline and L-proline-derived organocatalysts to activate both aldehydes and allenamides respectively. With this strategy we were able to build all-carbon quaternary stereocenters with moderate yield and enantioselectivity. In some cases certain additives were necessary to modulate the selectivity.