Homochiral Perfluoroalkyl-Group-Substituted Secondary Alcohols Through Stereoselective Reduction of Perfluoroalkyl 1-(<i>p</i>-Tolylsulfinyl)alkyl Ketones

Abstract

The reduction of some enantiomerically pure perfluoroalkyl α-(p-tolylsulfinyl) ketones was performed. Alcohols containing perfluoroalkyl and p-tolylsulfinyl groups were obtained with high diastereoselection when a phenyl residue was present on the sulfinylated carbon and with lower diastereoselection in the other cases. Removal of the chiral sulfinyl group from single diastereoisomers gave secondary alcohols containing a perfluoroalkyl group in enantiomerically pure form.