Povarov Reaction of Cycloiminium Formed in Situ via Hydroamination Cycloisomerization of Homopropargylic Amines with Electron-Rich Olefins

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• 作者：Qiangqiang Liu ; Chan Wang ; Qiang Li ; Yajie Hou ; Ye Wu ; Lingyan LiuWeixing Chang ; Jing Li
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：82
• 期：2
• 页码：950-958
• 全文大小：523K
• ISSN：1520-6904

文摘

A new, one-pot cascade reaction of homopropargylic amines with electron-rich olefins is developed in the presence of Cu(OTf)₂ and affords a series of octahydrofuro[3,2-c]pyrrolo[1,2-a]quinoline derivatives in yields of 38–80%. This reaction proceeds through an intramolecular hydroamination cyclization of homopropargylic amine to generate a highly reactive cycloenamine intermediate in situ that subsequently isomerizes to the cycloiminium cation followed by the Povarov-type reaction with dihydrofuran, dihydropyran, or dihydropyrrole. Notably, the Al₂O₃ additive plays a key role for the effective inhibition of competitive self-dimerization of homoproargylic amines.