3-Fluorotetrahydropyran-4-one derivatives from homopropargyl acetal

A one-pot gold(I)-catalysed regioselective method for the preparation of 3-fluoro-tetrahydropyran-4-one derivatives from homopropargyl acetal is described. The transformation is based on a Petasis-Ferrier rearrangement and a subsequent electrophilic fluorination. The 3-fluoro-pyran-4-one product acts as a protected precursor of alkylfluoro-α,β-(E)-unsaturated ketone.