Aminotellurinylation of Olefins and Its Utilization for Synthesis of 2-Oxazolidinones

Article abstract of DOI:10.1021/jo00279a031

Benzenetellurinyl acetate or trifluoroacetate in combination with ethyl carbamate effected regio- and stereoselective aminotellurinylation of olefins in the presence of boron trifluoride etherate in chloroform under reflux to give ethyl <(2-phenyltellurinyl)alkyl>carbamates in high yields.Benzenetellurinyl trifluoromethanesulfonate similarly did it even at the lower temperature of refluxing dichloromethane without Lewis acid.This reaction was successfully extended to cyclofunctionalization of olefinic carbamates into nitrogen heterocycles.Furthermore, when the aminotellurinylation was carried out in refluxing 1,2-dichloroethane, 2-oxazolidinone was obtained in a high yield.A mechanism of addition followed by intramolecular substitution in proposed on the basis of the stereochemistry of 2-oxazolidinone derivatives.