Transition Metal-Catalyzed Regioselective and Stereoselective Aminochlorination of Cinnamic Esters

A new aminohalogenation process has been developed for the synthesis of vicinal haloamine derivatives using cinnamic esters as substrates. The reaction was performed in CH 3 CN using ZnCl 2 or Cu(OTf) 2 as catalyst and N, N -dichloro- p -toluenesulfonamide as chlorine/nitrogen source. Good to excellent yields and regio- and stereoselectivities have been obtained. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.