title: Povarov Reaction of Cycloiminium Formed in Situ via Hydroamination Cycloisomerization of Homopropargylic Amines with Electron-Rich Olefins.
abstract: A new, one-pot cascade reaction of homopropargylic amines with electron-rich olefins is developed in the presence of Cu(OTf)2and 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 Al2O3additive plays a key role for the effective inhibition of competitive self-dimerization of homoproargylic amines.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Qiangqiang
authors.initials: Q
authors.lastname: Liu
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Chan
authors.initials: C
authors.lastname: Wang
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Li
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Yajie
authors.initials: Y
authors.lastname: Hou
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Ye
authors.initials: Y
authors.lastname: Wu
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Lingyan
authors.identifier: 0000-0001-5268-5986
authors.initials: L
authors.lastname: Liu
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Weixing
authors.initials: W
authors.lastname: Chang
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, the College of Chemistry, Nankai University , Tianjin 300071, China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Weijin Road 94, Nankai District, Tianjin 300071, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Li