Metalloporphyrins as new catalysts in the mild, efficient and regioselective conversion of epoxides to β-hydroxy thiocyanates with NH4SCN

Abstract

The regioselective cleavage of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanates in the presence of some metalloporphyrins has been studied. The epoxides were subject to cleavage by NH₄SCN in the presence of these catalysts under mild reaction conditions in various aprotic solvents. In this study, reagents and conditions have been discovered with which the individual β-hydroxy thiocyanates (useful intermediates toward biological active molecules) can be synthesized in high yield and with greater than 90% regioselectivity.