Diastereoselective Synthesis of Fluorinated Cyclopentene Derivatives

Significance

The interest in introducing the gem-difluoromethylene group in biologically active compounds arises from important changes in physical, chemical and biological properties. The introduction of such a group into carbocyclic nucleosides has however been impeded by the lack of a suitable method allowing fluorine atom incorporation. The authors have taken advantage of the ease of esterifying allylic alcohols with chloro­difluoroacetic acid to incorporate a CF₂ group in a carbocyclic structure. The products 2 obtained after Reformatsky-Claisen cascade were further elaborated to obtain the desired nucleosidic target 6.