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

Department of Chemistry

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

15 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6031-6034
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	17
DOIs	https://doi.org/10.1021/jo101148e
Publication status	Published - 2010 Sept 3

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo101148e

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@article{4cf64002c548441d8c998c246b2e7ad2,

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,

day = "3",

doi = "10.1021/jo101148e",

language = "English",

volume = "75",

pages = "6031--6034",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

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TY - JOUR

T1 - 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

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

Y1 - 2010/9/3

N2 - (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.

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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U2 - 10.1021/jo101148e

DO - 10.1021/jo101148e

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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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

Abstract

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CCDC 813658: Experimental Crystal Structure Determination

CCDC 813654: Experimental Crystal Structure Determination

CCDC 813655: Experimental Crystal Structure Determination

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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

Abstract

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CCDC 813658: Experimental Crystal Structure Determination

CCDC 813654: Experimental Crystal Structure Determination

CCDC 813655: Experimental Crystal Structure Determination

Cite this