Trifluoromethanesulfonic acid-catalyzed tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis reaction of arylpropagylsulfonamide- tethered 2,3-epoxycyclohexan-1-ols to spiropiperidines

Ming Nan Lin, Shih Hui Wu, Ming-Chang P. Yeh

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A simple and efficient trifluoromethanesulfonic acid-catalyzed cycloisomerization of arylpropagylsulfonamide-tethered 2,3-epoxycyclohexan-1-ols is described. The cyclization proceeds via tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis to afford spiropiperidines under mild reaction conditions.

Original languageEnglish
Pages (from-to)3290-3294
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number18
DOIs
Publication statusPublished - 2011 Dec 1

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Keywords

  • alkyne/aldehyde metathesis
  • semi-pinacol rearrangement
  • spiropiperidines
  • tandem reactions
  • triflic acid

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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