title: Asymmetric phase-transfer-catalyzed conjugate addition of glycine imine to exocyclic α,β-unsaturated ketones: construction of polycyclic imines containing three stereocenters.
abstract: We developed a facile, one-pot, multistep transformation between glycine imine and exocyclic α,β-unsaturated ketones in reactions catalyzed by chiral phase-transfer catalysts (PTC). A series of polycyclic imines containing three adjacent stereocenters were obtained in good to high yields with high diastereo- and enantioselectivities. Further transformation of the imines could afford N-fused polycyclic compounds with four adjacent stereocenters.
authors.affiliation: Department of Chemistry, Tianjin University, Tianjin 300072, P. R. China.
authors.forename: Jing
authors.initials: J
authors.lastname: Nie
authors.forename: Ming-Qing
authors.initials: MQ
authors.lastname: Hua
authors.forename: Heng-Ying
authors.initials: HY
authors.lastname: Xiong
authors.forename: Yan
authors.initials: Y
authors.lastname: Zheng
authors.forename: Jun-An
authors.initials: JA
authors.lastname: Ma
mesh_terms: D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D007659:Ketones; D011083:Polycyclic Compounds; D005998:Glycine