Synthesis of enantiomerically pure 4-acetoxy-2-fluoro-2-cyclopenten-1-one

Article abstract of DOI:10.1016/0957-4166(94)80047-2

Addition of molecular fluorine to cis-2-cyclopentene-1,4-diol gave the cis-anti adduct stereoselectively. This meso diol was dissymmetrized by means of acetylation under lipase catalysis to afford the monoacetate with a high enantiomeric purity. Oxidation of the monoacetate followed by elimination of hydrogen fluoride under basic conditions furnished the titled compound which is an attractive building block for chiral fluorinated molecules.