Monleon, AliciaBlay, GonzaloDomingo, Luis R.Muñoz Roca, María del CarmenPedro, José R.2014-11-122013-10-250947-6539https://riunet.upv.es/handle/10251/44095A very efficient synthesis of 5-halogen-1,3-oxazin-2-ones has been accomplished by the halocyclisation reaction of chiral nonracemic N-carbobenzyloxy (N-Cbz)-protected propargylic amines by using I-2, Br-2 and Cl-2 as electrophile sources. The nature of the halogen influences the reaction time and yield. However, in all cases the reaction is totally regioselective taking place through a 6-endo-dig process regardless of the nature of the halogen and of the substituents in the starting material. To rationalise the experimental results, theoretical studies at the B3LYP/6-311G* level have been performed.Reserva de todos los derechosDensity functional calculationsHalocyclisationOxazinonesPropargylic aminesReaction mechanismsRegioselectivityFISICA APLICADAArtículo10.1002/chem.201302089Cerrado