Efficient ring opening reactions of N-tosyl aziridines with amines and water in presence of catalytic amount of cerium(IV) ammonium nitrate

Abstract

While methyl- and benzylamines opened N-tosyl aziridines 1 very efficiently in acetonitrile with complete regio- and stereoselectivity to give the corresponding diamines 2 and 3, respectively, in excellent yields, similar openings with water could only be achieved in the presence of a catalytic amount of cerium(IV) ammonium nitrate under very mild conditions furnishing the amino alcohols 4.