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

doi:10.1002/adsc.201100576

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

22 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 language	English
Pages (from-to)	3290-3294
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	353
Issue number	18
DOIs	https://doi.org/10.1002/adsc.201100576
Publication status	Published - 2011 Dec

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201100576

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Trifluoromethanesulfonic acid-catalyzed tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis reaction of arylpropagylsulfonamide- tethered 2,3-epoxycyclohexan-1-ols to spiropiperidines. / Lin, Ming Nan; Wu, Shih Hui; Yeh, Ming-Chang P.

In: Advanced Synthesis and Catalysis, Vol. 353, No. 18, 12.2011, p. 3290-3294.

Research output: Contribution to journal › Article › peer-review

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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",

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AU - Wu, Shih Hui

AU - Yeh, Ming-Chang P.

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

Abstract

Keywords

ASJC Scopus subject areas

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