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

par Berger, Gilles ;Gelbcke, Michel ;Cauet, Emilie ;Luhmer, Michel ;Neve, Jean ;Dufrasne, François
Référence Tetrahedron letters, 54, 6, page (545-548)
Publication Publié, 2013-02-06

Article révisé par les pairs

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Résumé :

A new method for the synthesis of 15N-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-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.