title: Asymmetric synthesis of 2,3-dihydropyrroles by ring-opening/cyclization of cyclopropyl ketones using primary amines.
abstract: The asymmetric ring-opening/cyclization of cyclopropyl ketones with primary amine nucleophiles was catalyzed by a chiral N,N'-dioxide/scandium(III) complex through a kinetic resolution process. A broad range of cyclopropyl ketones and primary amines are suitable substrates of this reaction. The corresponding products were afforded in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield) under mild reaction conditions. This method provides a promising access to chiral 2,3-dihydropyrroles as well as an effective procedure for the kinetic resolution of 2-substituted cyclopropyl ketones.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Yong
authors.initials: Y
authors.lastname: Xia
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Haifeng
authors.initials: H
authors.lastname: Zheng
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012538:Scandium / Q000737:chemistry
chemical_list: D000588:Amines; D007659:Ketones; D010087:Oxides; D011758:Pyrroles; C013231:pyrroline; D012538:Scandium
keywords: N,N′-dioxides; cyclization; kinetic resolution; ring opening; scandium