RESUMEN
Enantiopure morpholine derivatives have been prepared by selenocyclofunctionalization of chiral 3-allyl-2-hydroxymethyl-substituted perhydro-1,3-benzoxazine derivatives. The cyclization occurs in high yields and diastereoselection, although the temperature of the reaction and the structure of the substituent at C-2 and the substitution pattern of the double bond can modify the regio- and stereochemistry of the final products.
RESUMEN
Regio- and diastereoselective methoxyselenenylation of cinnamylamines attached to a chiral perhydrobenzoxazine occurs in high yields by reaction with benzeneselenenyl chloride in dichloromethane-methanol. The diastereoselection is dependent on the temperature of the reaction and the structure of the substituent at C-2 and can be rationalized by accepting a 1,4-asymmetric induction process after coordination of the selenium to the nitrogen atom of the allylamine system.
Asunto(s)
Benzoxazinas/química , Nitrógeno/química , Compuestos de Organoselenio/síntesis química , Selenio/química , Conformación Molecular , Compuestos de Organoselenio/química , EstereoisomerismoRESUMEN
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.