title: Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles.
abstract: An enantioselective α-oxyamination of unprotected 3-substituted oxindoles with nitrosobenzene catalyzed by tertiary amine-thiourea bifunctional organocatalysts has been developed and affords the corresponding 3-amino-2-oxindole derivatives in good yields and with moderate to excellent enantioselectivities (up to > 99.9 : 0.1 er when the product is isolated by direct filtration from the reaction mixture). The absolute configuration of the major enantiomers of the products has been established both by chemical correlation and by comparison between the theoretically calculated and the experimental ECD.
authors: Departament de Química Orgànica, Universitat de Barcelona. Facultat de Química, C. Martí i Franquès 1-11, 08028, Barcelona, Spain.
authors: Xavier
authors: X
authors: Companyó
authors: Guillem
authors: G
authors: Valero
authors: Oriol
authors: O
authors: Pineda
authors: Teresa
authors: T
authors: Calvet
authors: Mercè
authors: M
authors: Font-Bardía
authors: Albert
authors: A
authors: Moyano
authors: Ramon
authors: R
authors: Rios
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D000078183:Oxindoles; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D000588:Amines; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D013890:Thiourea