title: Dynamic kinetic asymmetric ring-opening/reductive amination sequence of racemic nitroepoxides with chiral amines: enantioselective synthesis of chiral vicinal diamines.
abstract: We report a highly diastereoselective synthesis of vicinal diamines by the treatment of nitroepoxides with primary amines and then a reducing agent. When using a chiral primary amine, racemic nitroepoxides are transformed into chiral diamines as a single enantiomers (>95:5 er) through a dynamic kinetic asymmetric transformation (DYKAT). The overall process is a one-pot procedure combining the exposure of nitroepoxides to chiral amines to afford diastereomeric mixtures of aminoimines and subsequent stereoselective imine reduction.
authors: Departament de Química Inorgànica i Orgànica, Universitat Jaume I, 12080 Castelló, Spain.
authors: Juan
authors: J
authors: Agut
authors: Andreu
authors: A
authors: Vidal
authors: Santiago
authors: S
authors: Rodríguez
authors: Florenci V
authors: FV
authors: González
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000588:Amines; D004852:Epoxy Compounds