A novel stereoselective synthesis of cis-2-fluoro-cyclopropane-1-carboxylic acid

Article abstract of DOI:10.1016/0040-4039(96)01952-1

A novel method consisting four-step from tert-butyl acrylate (4) and chloromethyl phenyl sulfoxide (5) for preparing cis-2-fluorocyclopropane-1-carboxylic acid (cis-3) was elaborated. The method involves initial formation of the cis-2-phenylsulfinylcyclopropanecarboxylate (cis-6), fluorination by molecular fluorine to trans-7, reductive desulfonylation to the ester (cis-9) and acid-catalyzed hydrolysis to the final product (cis-3).