title: Catalytic asymmetric Tamura cycloadditions involving nitroalkenes.
abstract: The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.
authors.affiliation: School of Chemistry Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland. connons@tcd.ie.
authors.forename: Francesco
authors.initials: F
authors.lastname: Manoni
authors.affiliation: School of Chemistry Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland. connons@tcd.ie.
authors.forename: Umar
authors.initials: U
authors.lastname: Farid
authors.affiliation: School of Chemistry Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland. connons@tcd.ie.
authors.forename: Cristina
authors.identifier: http://orcid.org/0000-0001-9178-5146
authors.initials: C
authors.lastname: Trujillo
authors.affiliation: School of Chemistry Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland. connons@tcd.ie.
authors.forename: Stephen J
authors.identifier: http://orcid.org/0000-0003-2984-9246
authors.initials: SJ
authors.lastname: Connon