Triethylgallium as a nonnucleophilic base to generate enolates from ketones

Yoshio Nishimura, Yutaka Miyake, Ryo Amemiya, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)5077-5080
Number of pages4
JournalOrganic letters
Volume8
Issue number22
DOIs
Publication statusPublished - 2006 Oct 26

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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