1,4-asymmetric induction in methoxyselenenylation of double bonds at the nitrogen side of chiral perhydro-1,3-benzoxazines promoted by nonbonded Se...N interactions.
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.
Pedrosa
Rafael
R
Departamento de Química Organica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain. pedrosa@qo.uva.es
Andrés
Celia
C
Mendiguchía
Pilar
P
Nieto
Javier
J
D048588:Benzoxazines / Q000737:chemistry*; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism
D048588:Benzoxazines; D016566:Organoselenium Compounds; D012643:Selenium; D009584:Nitrogen