title: Regio- and stereoselective methoxyselenenylation of chiral 2-vinyl perhydro-1,3-benzoxazines promoted by selenium-heteroatom nonbonded interactions.
abstract: Regio- and diastereoselective methoxyselenenylations of double bonds attached to the N,O-ketalic carbon of chiral perhydrobenzoxazines occur in high yields by reaction with benzeneselenenyl chloride in dichloromethane-methanol. The diastereoselection is dependent on the reaction conditions and the structure of the starting compounds and can be rationalized by accepting the coordination of the selenium to the oxygen atom of the heterocycle.
authors.affiliation: Departamento de Química Organica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain. pedrosa@qo.uva.es
authors.forename: Rafael
authors.initials: R
authors.lastname: Pedrosa
authors.forename: Celia
authors.initials: C
authors.lastname: Andrés
authors.forename: Raquel
authors.initials: R
authors.lastname: Arias
authors.forename: Pilar
authors.initials: P
authors.lastname: Mendiguchía
authors.forename: Javier
authors.initials: J
authors.lastname: Nieto
mesh_terms: D048588:Benzoxazines / Q000737:chemistry*; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D048588:Benzoxazines; D016566:Organoselenium Compounds; D010078:Oxazines