Synthesis of α- and/or γ-benzoyloxy-α,β-enones from α-halo-α,β-enones

Yujiro Hayashi, Mitsuru Shoji, Satoshi Kishida

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Sodium benzoate reacts with α-halo-α,β-enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxylated α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent. Sodium benzoate reacts with α-halo-α,β- enones in the presence of tetrabutylammonium hydrogensulfate or 18-Crown-6 to afford α- and/or γ-benzoyloxy-α,β-enones in good yield. The α/γ and γ/γ′ selectivities are dependent on the substrate and reagent.

Original languageEnglish
Pages (from-to)681-685
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number4
DOIs
Publication statusPublished - 2005 Jan 24

Keywords

  • Ammonium salt
  • Crown ether
  • Enones
  • Substitution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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