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

Research output: Contribution to journalArticle

12 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 languageEnglish
Pages (from-to)6031-6034
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number17
DOIs
Publication statusPublished - 2010 Sep 3

ASJC Scopus subject areas

  • Organic Chemistry

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