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

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• 作者：Ming-Chang P. Yeh ; Ming-Nan Lin ; Wei-Jong Chang ; Jia-Lun Liou ; Ya-Fon Shih
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：September 3, 2010
• 年：2010
• 卷：75
• 期：17
• 页码：6031-6034
• 全文大小：751K
• 年卷期：v.75,no.17(September 3, 2010)
• ISSN：1520-6904

文摘

(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.