Tetrahedron letters

Synthesis of chiral vicinal C 2 symmetric and unsymmetric bis (sulfonamide) ligands based on trans-1, 2-cyclohexanediamine by aminolysis of N-tosylaziridines

A Bisai, BAB Prasad, VK Singh

Index: Bisai, Alakesh; Prasad, B.A. Bhanu; Singh, Vinod K. Tetrahedron Letters, 2005 , vol. 46, # 46 p. 7935 - 7939

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Citation Number: 19

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 of chiral vicinal C2 symmetric bis (sulfonamide) and unsymmetrical bis (sulfonamide) ligands based on trans-1, 2- ...