Equatorial preference in the GaCl3-promoted ethenylation of cyclic ketones

M. Arisawa, C. Miyagawa, M. Yamaguchi

Research output: Contribution to journalReview articlepeer-review

19 Citations (Scopus)

Abstract

Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl3. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave β-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.

Original languageEnglish
Pages (from-to)138-145
Number of pages8
JournalSynthesis
Issue number1
DOIs
Publication statusPublished - 2002

Keywords

  • Cyclic ketone
  • Equatorial
  • Silylethyne
  • α-ethenylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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