NUCLEOPHILIC α-SUBSTITUTED ORGANOMETALLIC REAGENTS IN HOMOLOGATION CHEMISTRY: SYNTHETIC APPLICATIONS AND BIOLOGICAL PERSPECTIVES

The homologation chemistry pertains the possibility of obtaining from an organic substrate with n carbon atoms, the corresponding homologue with n + 1 carbon atoms and, among the most useful methods to obtain such derivatives, organometallic chemistry occupies a prominent role. The aim of this PhD thesis is to provide a detailed overview of the new methodologies developed for the homologation of organic substrates using organometallic reagents such as lithium halocarbenoids and potassium halocarbanion, mainly implicated in the synthesis of halodrins, primary alkyl halides, fluoromethylketones and difluoromethyl ketones. Because of the great importance of fluoroketones associated to the Medicinal Chemistry, the synthesis of difluoromethylketones has been applied to the design and development of peptide difluoromethylketones as new reversible/irreversible cysteine protease inhibitors.