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Synthesis 1988; 1988(12): 955-960
DOI: 10.1055/s-1988-27764
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Homochiral Perfluoroalkyl-Group-Substituted Secondary Alcohols Through Stereoselective Reduction of Perfluoroalkyl 1-(p-Tolylsulfinyl)alkyl Ketones

Pierfrancesco Bravo* , Massimo Frigerio, Giuseppe Resnati
  • *CNR - Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico, Piazza Leonardo da Vinci 32, I-20133 Milano, Italy
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Publication Date:
20 August 2002 (online)

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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.