Copper-Catalyzed Cascade Reaction via Intramolecular Hydroamination Cyclization of Homopropargylic Amines and Intermolecular Povarov Reaction with Imines

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• 作者：Hongkai Wang ; Chan Wang ; Kaimeng Huang ; Lingyan Liu ; Weixing Chang ; Jing Li
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2367-2370
• 全文大小：357K
• 年卷期：0
• ISSN：1523-7052

文摘

A new one-pot cascade reaction of homopropargylic amines with simple imines is developed in the presence of Cu(OTf)₂ and affords a series of hexahydro-1H-pyrrolo[3,2-c]quinoline derivatives in good to high yields. This reaction proceeds through an intramolecular hydroamination cyclization of homopropargylic amine to generate a highly reactive dihydropyrrole intermediate in situ. It subsequently reacts with imine via an intermolecular inverse-electron-demand aza-Diels–Alder reaction and a 1,3-H shift to give the fused pyrroloquinoline structures, forming two new C–C bonds and one C–N bond and one N–H bond.