Divergent Reaction of Activated Pyridines with α,α-Difluorinated gem -Diols: Regioselective Synthesis of gem -Difluorinated Dihydropyridines and Dihydropyridones.

The nucleophilic reactivity of α,α-difluorinated gem -diols toward activated pyridinium salts has been capitalized in a highly regioselective fashion, offering biologically relevant 1,4-dihydropyridines and 3,4-dihydro-2-pyridones adorned with the valuable gem -difluoromethylene motif. The protocol is scalable as well as high yielding and accommodates a broad range of substrates and functional groups. Additionally, the synthesis of difluorinated oxa-azabicyclo[3.3.1]nonane frameworks has been showcased through product diversification.