A stereoselective preparation of 1-fluorocyclopropane-1-carboxylate derivatives through radical addition of fluoroiodoacetate to alkenes followed by intramolecular substitution reaction

Triethylborane mediated iodine atom-transfer radical addition of fluoroiodoacetate to 1-alkene or cyclic alkene proceeded in a good yield to give the α-fluoro-γ-iodo esters in non-diastereoselective manner, while the subsequent cyclopropane formation via enolate of the α-fluoro ester provided the corresponding fluorocyclopropanecarboxylate in a highly cis- or F-endo-selective manner.