Rhenium(I)-catalyzed cyclization of silyl enol ethers containing a propargyl carboxylate moiety: Versatile access to highly substituted phenols

Kodai Saito, Yuji Onizawa, Hiroyuki Kusama, Nobuharu Iwasawa

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Selective migration: The rhenium-catalyzed reaction of 2-siloxy-1-en-5-ynes containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols. (Chemical Equation Presented)

Original languageEnglish
Pages (from-to)4716-4720
Number of pages5
JournalChemistry - A European Journal
Volume16
Issue number16
DOIs
Publication statusPublished - 2010 Apr 26
Externally publishedYes

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Keywords

  • Alkynes
  • Cycloaddition
  • Elimination
  • Phenols
  • Rhenium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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