Abstract
Starting from the secondary alcohols 1, cyclohexanols 2 having three (XF) of four (XCl) chiral centres on the ring can be obtained in optically pure form by intramolecular trapping of difluoroalkyl or chlorofluoroalkyl radicals (tributyltin hydride method). ▪ The diastereoselection of the process seems to be determined mainly by the stereochemistry at the carbons bearing the sulfinyl and the hydroxyl substituents. Optically pure difluoro- or chloro, fluoro-cyclopentanols can be obtained in the same way.
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