Synthesis of Enantiomerically Pure Fluoro- and gem-Chlorofluorocyclohexane Derivatives

gem-Chlorofluorocyclohexanols 10 are prepared in good yields by radical-promoted cyclization from the corresponding w-dichlorofluoroheptenols 4. Fluorocyclohexanols 11 are obtained either from 10 or in a single step from open-chain alcohols 4. The stereochemical outcome of both the radical cyclization and the reductive dechlorination is discussed. Elimination of the chiral auxiliary sulfinyl group and appropriate elaborations afford enantiomerically pure derivatives 12- 17. Relative and absolute configurations as well as preferred conformations in solution for all final compounds are provided