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 | |
| Publication status | Published - 2010 Sep 3 |
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Yeh, M-C. P., Lin, M. N., Chang, W. J., Liou, J. L., & Shih, Y. F. (2010). 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. Journal of Organic Chemistry, 75(17), 6031-6034. https://doi.org/10.1021/jo101148e