Triethylgallium as a Nonnucleophilic Base to Generate Enolates from Ketones

Triethylgallium deprotonated cyclic and acyclic ketones at 125−175 °C without forming carbonyl addition products, and the resulting gallium enolates underwent facile C-benzoylation and an aldol reaction. Unsymmetrical ketones were preferentially enolized at the methylene moiety, which was under kinetic control.