Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening

A reactant economizing process for the regioselective aminolysis of epoxides using equimolar quantities of reactants catalyzed by the double hydrogen bond donor N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is reported. Regioselectivity of the reaction is controlled by the electronic nature of the substituent on the styrene oxide, which has been substantiated on the basis of 13C NMR data and DFT calculations.