Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors

The synthesis of gem-difluorinated beta-lactams and gem-difluorinated beta-amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for beta-lactams) or N-(alpha-aminoalkyl) benzotriazoles (for beta-amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxy-peptidase inhibitors. N-Alkylation and N-acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).