1240184-18-2Relevant academic research and scientific papers
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
Yeh, Ming-Chang P.,Lin, Ming-Nan,Chang, Wei-Jong,Liou, Jia-Lun,Shih, Ya-Fon
body text, p. 6031 - 6034 (2010/11/17)
(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.
