Abstract
The intermolecular α-allylation of enals and enones occurs by the condensation of variously substituted allenamides with allylic alcohols. Cooperative catalysis by [Au(ItBu)NTf2] and AgNTf2 enables the synthesis of a range of densely functionalized α-allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an α-gold(I) enal/enone as the active nucleophilic species.
A golden ally in allylation: In a gold(I)-assisted formal α-allylation of acrylaldehyde, enones, and acyl silanes with alcohols, allenamides were used as precursors to intermediate α-gold-substituted unsaturated carbonyl compounds. The transformation enabled the synthesis of a diverse range of products under mild conditions (see scheme; ItBu=1,3-di(tert-butyl)imidazol-2-ylidene).