title: The cycloaddition of nitrones with homochiral cyclopropanes.
abstract: The cycloaddition of nitrones and enantiomerically pure cyclopropane-1,1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitution. Optically active 2-substituted cyclopropane-1,1-dicarboxylates are shown to racemize under typical reaction conditions, providing evidence for a zwitterionic ring-opened intermediate.
authors.affiliation: Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
authors.forename: Katarina
authors.initials: K
authors.lastname: Sapeta
authors.forename: Michael A
authors.initials: MA
authors.lastname: Kerr
mesh_terms: D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D009589:Nitrogen Oxides; C015388:nitrones