title: Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones.
abstract: N-Aryl 4-methylene-2-oxazolidinones, prepared via the corresponding O-propargyl carbamates, underwent nitrile oxide cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.
authors.affiliation: CSIRO Materials Science and Engineering, Private Bag 10, Clayton South MDC, Vic 3169, Australia.
authors.forename: Sarah L
authors.initials: SL
authors.lastname: Harding
authors.forename: G Paul
authors.initials: GP
authors.lastname: Savage
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis; D003500:Cyclization; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D009570:Nitriles; D023303:Oxazolidinones; D010087:Oxides