Triethylgallium as a nonnucleophilic base to generate enolates from ketones.
Triethylgallium deprotonated cyclic and acyclic ketones at 125-175 degrees 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. [reaction: see text]
Nishimura
Yoshio
Y
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan.
Miyake
Yutaka
Y
Amemiya
Ryo
R
Yamaguchi
Masahiko
M