Organic letters

Triethylgallium as a nonnucleophilic base to generate enolates from ketones

…, Y Miyake, R Amemiya, M Yamaguchi

Index: Nishimura, Yoshio; Miyake, Yutaka; Amemiya, Ryo; Yamaguchi, Masahiko Organic Letters, 2006 , vol. 8, # 22 p. 5077 - 5080

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Citation Number: 20

Abstract

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.