Substrate-dependent fluorinations of highly functionalized cycloalkanes

Substrate-dependent fluorinations of several highly functionalized cycloalkanes with multiple stereocentres were investigated. The synthetic transformations were based on selective functionalization of the ring C]C bonds of the readily available bicyclic b-lactams by epoxidation and regioselective nucleophilic oxirane opening with azide or cyanide, followed by hydroxyefluorine exchange with Deoxofluor. Depending on the substituents and their relative steric arrangement, the attempted fluorinations produced different types of substituted cycloalkanes. These selective, substrate-directed synthetic procedures and their presumed pathways towards interesting highly functionalized fluorinated cycloalkane scaffolds were investigated