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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

27 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	3290-3294
頁數	5
期刊	Advanced Synthesis and Catalysis
卷	353
發行號	18
DOIs	https://doi.org/10.1002/adsc.201100576
出版狀態	已發佈 - 2011 12月

ASJC Scopus subject areas

催化
有機化學

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10.1002/adsc.201100576

其它文件與鏈接

CCDC 835096: Experimental Crystal Structure Determination
Lin, M.-N. (Creator), Wu, S.-H. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2012
DOI: 10.5517/ccx0zlg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccx0zlg&sid=DataCite
資料集: Dataset
CCDC 835097: Experimental Crystal Structure Determination
Lin, M.-N. (Creator), Wu, S.-H. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2012
DOI: 10.5517/ccx0zmh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccx0zmh&sid=DataCite
資料集: Dataset

引用此

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.
於: Advanced Synthesis and Catalysis, 卷 353, 編號 18, 12.2011, p. 3290-3294.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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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.\}",

year = "2011",

month = dec,

doi = "10.1002/adsc.201100576",

language = "English",

volume = "353",

pages = "3290--3294",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

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

Y1 - 2011/12

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

UR - https://www.scopus.com/pages/publications/84255177581

UR - https://www.scopus.com/pages/publications/84255177581#tab=citedBy

U2 - 10.1002/adsc.201100576

DO - 10.1002/adsc.201100576

M3 - Article

AN - SCOPUS:84255177581

SN - 1615-4150

VL - 353

SP - 3290

EP - 3294

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 18

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 835096: Experimental Crystal Structure Determination

CCDC 835097: Experimental Crystal Structure Determination

引用此