Regio- and stereoselective methoxyselenenylation of chiral 2-vinyl perhydro-1,3-benzoxazines promoted by selenium-heteroatom nonbonded interactions

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.