| In palladium-catalyzed alpha-allylation, two endemic problems are epimerization at the alpha-carbon of carbonyl function groups and non-specific generation of the enolate isomer. To solve these challenges in a novel way, palladium catalyzed allylation was combined with C1-ammonium enolates in a cooperative catalysis framework. Simultaneous activation of both the nucleophile and the electrophile allows for the development of unique reactivity. The reaction presented employs a rebound leaving group and is shown to work with different substituents on the phenyl ring of the nucleophile (14 examples with 85-93% ee). |
