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 |
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Pages (from-to) | 6031-6034 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 75 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2010 Sep 3 |
ASJC Scopus subject areas
- Organic Chemistry