title: Catalytic intermolecular alkene oxyamination with nitrenes.
abstract: The Rh(II)-catalyzed intermolecular addition of nitrenes to aromatic and aliphatic alkenes provides vicinal amino alcohols with yields of up to 95 % and complete regioselectivity. This 1,2-oxyamination reaction involves the formation of an aziridine intermediate that undergoes in situ ring opening. The latter is induced by the Rh-bound nitrene that behaves as a Lewis acid.
authors.affiliation: Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France).
authors.forename: Geoffroy
authors.initials: G
authors.lastname: Dequirez
authors.forename: Jennifer
authors.initials: J
authors.lastname: Ciesielski
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Philippe
authors.initials: P
authors.lastname: Dauban
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D002384:Catalysis; D006900:Hydroxylation; D007097:Imines / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000605:Amino Alcohols; D001388:Aziridines; D007097:Imines; C017621:phenylnitrene; C033132:aziridine; D012238:Rhodium
keywords: alkenes; aminohydroxylation; nitrenes; rhodium; synthetic methods