Aminolysis of N-tosylaziridines: an approach to asymmetric synthesis of symmetric and unsymmetric chiral sulfonamide ligands

Abstract

The ring-opening of N-tosylaziridines with aliphatic amines can be efficiently catalyzed by lithium perchlorate to provide derivatives of the trans-1,2-diamine in high yields. The reaction was used in desymmetrization of several cyclic N-tosylaziridines using chiral amines. Using this strategy, an efficient synthesis was developed of chiral vicinal C₂ symmetric bis-(sulfonamides), unsymmetrical bis(sulfonamides) and other symmetric and unsymmetric ligands based on trans-1,2-cyclohexanediamine.