title: 7-endo selenocyclization reactions on chiral 3-prenyl and 3-cinnamyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives. A way to enantiopure 1,4-oxazepanes.
abstract: Enantiopure 1,4-oxazepane derivatives have been prepared by selenocyclofunctionalization of chiral 3-prenyl- and 3-cinnamyl-2-hydroxymethyl-substituted perhydro-1,3-benzoxazine derivatives. The 7-endo-cyclization occurs in high yields and diastereoselection. The regio- and stereochemistry of the cyclization products was dependent on the substitution pattern of the double bond, the nature of the hydroxyl group and the experimental conditions.
authors.affiliation: Instituto CINQUIMA and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Paseo de Belén, 7, 47011 Valladolid, Spain. javiernr@qo.uva.es.
authors.forename: Javier
authors.initials: J
authors.lastname: Nieto
authors.forename: Celia
authors.initials: C
authors.lastname: Andrés
authors.forename: Alfonso
authors.initials: A
authors.lastname: Pérez-Encabo
mesh_terms: D048588:Benzoxazines / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009387:Neoprene / Q000737:chemistry*; D010077:Oxazepines / Q000138:chemical synthesis*; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D048588:Benzoxazines; D010077:Oxazepines; C016077:prenyl; D009387:Neoprene; D012643:Selenium