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

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] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes.