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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Alkynes
Cyclization
Aldehydes
Acids
trifluoromethanesulfonic acid

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Trifluoromethanesulfonic acid-catalyzed tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis reaction of arylpropagylsulfonamide- tethered 2,3-epoxycyclohexan-1-ols to spiropiperidines",
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.",
keywords = "alkyne/aldehyde metathesis, semi-pinacol rearrangement, spiropiperidines, tandem reactions, triflic acid",
author = "Lin, {Ming Nan} and Wu, {Shih Hui} and Yeh, {Ming-Chang P.}",
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T1 - Trifluoromethanesulfonic acid-catalyzed tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis reaction of arylpropagylsulfonamide- tethered 2,3-epoxycyclohexan-1-ols to spiropiperidines

AU - Lin, Ming Nan

AU - Wu, Shih Hui

AU - Yeh, Ming-Chang P.

PY - 2011/12/1

Y1 - 2011/12/1

N2 - 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.

AB - 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.

KW - alkyne/aldehyde metathesis

KW - semi-pinacol rearrangement

KW - spiropiperidines

KW - tandem reactions

KW - triflic acid

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U2 - 10.1002/adsc.201100576

DO - 10.1002/adsc.201100576

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EP - 3294

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

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