Synthesis of α,α‐Difluoro‐β‐amino Esters or gem ‐Difluoro‐β‐lactams as Potential Metallocarboxypeptidase Inhibitors

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