title: Enantioselective Synthesis of Spirobarbiturate-Cyclohexenes through Phosphine-Catalyzed Asymmetric [4 + 2] Annulation of Barbiturate-Derived Alkenes with Allenoates.
abstract: An enantioselective synthesis of pharmaceutically important spirobarbiturates has been achieved via spirocyclic chiral phosphine-catalyzed asymmetric [4 + 2] annulation of barbiturate-derived alkenes with allenoates. With the use of this tool, various spirobarbiturate-cyclohexenes are obtained in good to excellent yields with excellent diastereo- and enantioselectivities. A wide range of α-substituted allenoates and barbiturate-derived alkenes were tolerated.
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Honglei
authors.initials: H
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Chunhao
authors.initials: C
authors.lastname: Yuan
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Guo-Peng
authors.initials: GP
authors.lastname: Wang
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Shou-Fei
authors.initials: SF
authors.lastname: Zhu
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Wu
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Zhanhu
authors.initials: Z
authors.lastname: Sun
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Yumei
authors.initials: Y
authors.lastname: Xiao
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, P. R. China.
authors.forename: Hongchao
authors.initials: H
authors.lastname: Guo
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001463:Barbiturates; D053138:Cyclohexenes; D010720:Phosphines; D013141:Spiro Compounds; C044646:phosphine