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

• DOI: 10.1016/j.tetlet.2012.11.079
• Publication Date: 2012-11-29T05:46:15Z
• Authors: Gilles Berger; Michel Gelbcke; Emilie Cauët; Michel Luhmer; Jean Nève; François Dufrasne
• Keywords: Diastereomer; Vicinal; Benzylamine; Piperidine

Abstract A new method for the synthesis of 15 N-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. 15 N was introduced by means of [ 15 N]-benzylamine, prepared from 15 NH 4 Cl. The final compounds are highly valuable because [ 1 H– 15 N] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes.