Efficient Ring Opening Reactions of <i>N</i>-Tosyl Aziridines with Amines and Water in Presence of Catalytic Amount of Cerium(IV) Ammonium Nitrate

Abstract

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.