Cyclization and fluorination of 5-hexenols with boron trifluoride etherate. Stereoselective synthesis of (optically active) fluorinated cyclohexane derivatives by cyclization of ω-pentenyl pentadienol tricarbonyl iron complexes

Article abstract of DOI:10.1016/S0040-4039(99)01797-9

Monofluorinated cyclohexane derivatives are obtained by treatment of ω-pentenyl pentadienol tricarbonyl iron complexes with boron trifluoride etherate. The reaction is stereoselective, so that optically active fluorocyclohexanes can be obtained from readily available enantiomerically pure starting complexes. This fluorocyclization reaction with the cheap reagent BF₃.Et₂O is not restricted to transition-metal coordinated substrates, working also with simple ω-pentenyl benzylic alcohols.