4.8 Article

Triethylgallium as a nonnucleophilic base to generate enolates from ketones

Journal

ORGANIC LETTERS
Volume 8, Issue 22, Pages 5077-5080

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol061948m

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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.

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