Synthesis of cis -3-acyl-4-alkenylpyrrolidines via Gold(I)-catalyzed cycloisomerization reaction of (Z)-8-aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols

Ming Chang P. Yeh; Ming Nan Lin; Wei Jong Chang; Jia Lun Liou; Ya Fon Shih

doi:10.1021/jo101148e

Synthesis of cis -3-acyl-4-alkenylpyrrolidines via Gold(I)-catalyzed cycloisomerization reaction of (Z)-8-aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols

Ming Chang P. Yeh
, Ming Nan Lin
, Wei Jong Chang
, Jia Lun Liou
, Ya Fon Shih

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

16 引文斯高帕斯（Scopus）

摘要

(Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols were cycloisomerized to the corresponding cis-3-acyl-4-alkenylpyrrolidines when treated with a catalytic amount of Ph₃PAuCl/AgOTf in CH₂Cl₂. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate cis-3-acyl-4-alkenylpyrrolidines in good yields. This transformation can be applied to the synthesis of cis- and trans-3-acyl-4-alkenylcyclopentanes from (Z)- and (E)-8-aryloct-2-en-7-yn-1-ols, respectively.

原文	英語
頁（從 - 到）	6031-6034
頁數	4
期刊	Journal of Organic Chemistry
卷	75
發行號	17
DOIs	https://doi.org/10.1021/jo101148e
出版狀態	已發佈 - 2010 9月 3

ASJC Scopus subject areas

有機化學

存取文件

10.1021/jo101148e

其它文件與鏈接

CCDC 813658: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Lin, M.-N. (Creator), Chang, W.-J. (Creator), Liou, J.-L. (Creator) & Shih, Y.-F. (Creator), Unknown Publisher, 2011
DOI: 10.5517/ccw9p1w, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccw9p1w&sid=DataCite
資料集: Dataset
CCDC 813654: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Lin, M.-N. (Creator), Chang, W.-J. (Creator), Liou, J.-L. (Creator) & Shih, Y.-F. (Creator), Unknown Publisher, 2011
DOI: 10.5517/ccw9nxq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccw9nxq&sid=DataCite
資料集: Dataset
CCDC 813656: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Lin, M.-N. (Creator), Chang, W.-J. (Creator), Liou, J.-L. (Creator) & Shih, Y.-F. (Creator), Unknown Publisher, 2011
DOI: 10.5517/ccw9nzs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccw9nzs&sid=DataCite
資料集: Dataset

引用此

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title = "Synthesis of cis -3-acyl-4-alkenylpyrrolidines via Gold(I)-catalyzed cycloisomerization reaction of (Z)-8-aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols",

abstract = "(Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols were cycloisomerized to the corresponding cis-3-acyl-4-alkenylpyrrolidines when treated with a catalytic amount of Ph3PAuCl/AgOTf in CH2Cl2. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate cis-3-acyl-4-alkenylpyrrolidines in good yields. This transformation can be applied to the synthesis of cis- and trans-3-acyl-4-alkenylcyclopentanes from (Z)- and (E)-8-aryloct-2-en-7-yn-1-ols, respectively.",

author = "Yeh, \{Ming Chang P.\} and Lin, \{Ming Nan\} and Chang, \{Wei Jong\} and Liou, \{Jia Lun\} and Shih, \{Ya Fon\}",

year = "2010",

month = sep,

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doi = "10.1021/jo101148e",

language = "English",

volume = "75",

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AU - Yeh, Ming Chang P.

AU - Lin, Ming Nan

AU - Chang, Wei Jong

AU - Liou, Jia Lun

AU - Shih, Ya Fon

PY - 2010/9/3

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AB - (Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols were cycloisomerized to the corresponding cis-3-acyl-4-alkenylpyrrolidines when treated with a catalytic amount of Ph3PAuCl/AgOTf in CH2Cl2. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate cis-3-acyl-4-alkenylpyrrolidines in good yields. This transformation can be applied to the synthesis of cis- and trans-3-acyl-4-alkenylcyclopentanes from (Z)- and (E)-8-aryloct-2-en-7-yn-1-ols, respectively.

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Synthesis of cis -3-acyl-4-alkenylpyrrolidines via Gold(I)-catalyzed cycloisomerization reaction of (Z)-8-aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 813658: Experimental Crystal Structure Determination

CCDC 813654: Experimental Crystal Structure Determination

CCDC 813656: Experimental Crystal Structure Determination

引用此