α-Ethynylation reaction of ketones using catalytic amounts of trialkylgallium base

Yoshio Nishimura, Ryo Amemiya, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

Trialkylgalliums serve as a base to generate enolates from ketones. In the presence of catalytic amounts of a trialkylgallium (20-40 mol %) and 2,6-di(t-butyl)-4-methylpyridine (30-50 mol %), acyclic, and cyclic ketones were ethynylated at the α-carbon with chlorosilylethyne. The selective monoethynylation and diethynylation could be conducted for cyclic ketones by appropriate choices of the conditions, in which the addition of a catalytic amount of butyllithium (20-40 mol %) increased the yield.

Original languageEnglish
Pages (from-to)1839-1843
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number11
DOIs
Publication statusPublished - 2006 Mar 13

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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