Tetrahedron letters

Synthesis of 15 N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds

…, M Gelbcke, E Cauët, M Luhmer, J Nève, F Dufrasne

Index: Berger, Gilles; Gelbcke, Michel; Cauet, Emilie; Luhmer, Michel; Neve, Jean; Dufrasne, Francois Tetrahedron Letters, 2013 , vol. 54, # 6 p. 545 - 548

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Citation Number: 4

Abstract

A new method for the synthesis of 15N-labeled chiral β-diamines from a common precursor, either optically pure amino acids or anti-β-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. 15N was introduced by means of [15N]-benzylamine, prepared from 15NH4Cl. The final compounds are highly valuable because [1H–15N] ...