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J Org Chem. 2006 Mar 17;71(6):2424-8.

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

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  • 1Departamento de Química Organica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain.


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.

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