Late-stage fluorination of bridged scaffolds: Chemoselective generation of a CHF group at three positions of the bicyclo[3.3.1]nonane system

•Monofluorobicyclo[3.3.1]nonane derivatives have been synthesised.•Control of stereochemistry at many locations of the bridged core was achieved.•Introduction of fluorine is chemoselective.•Conformation of the bicyclo scaffold can control the products formed.•The major conformer was deduced for each fluorobicyclo compound prepared.