title: Total facial selectivity of a D-erythrosyl aromatic imine in [4π + 2π] cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines.
abstract: Different electron-rich dienophiles were combined with the imine obtained from 2,4-O-benzylidene-d-erythrose and p-anisidine furnishing enantiomerically pure tetrahydroquinolines, by inverse electron-demand [4π + 2π] cycloaddition. The imine was also reacted with 2-substituted electron-rich 1,3-butadienes giving the diastereomeric pure product, resulting from the normal electron demand cycloaddition. The facial selectivity of both processes is proposed on the basis of a 1,4-relationship between the hydroxyl group and the nitrogen atom in the chiral N-(p-methoxyphenyl)imine derivative.
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. mja@quimica.uminho.pt.
authors.forename: Juliana
authors.initials: J
authors.lastname: Ferreira
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. mja@quimica.uminho.pt.
authors.forename: Vera C M
authors.initials: VC
authors.lastname: Duarte
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. mja@quimica.uminho.pt.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Noro
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. mja@quimica.uminho.pt.
authors.forename: António
authors.initials: A
authors.lastname: Gil Fortes
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. mja@quimica.uminho.pt.
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Alves
mesh_terms: D061565:Cycloaddition Reaction; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D011804:Quinolines / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D007097:Imines; D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline