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No thorough study directed towards the optimization of the number of equivalents of the organolithium reagent involved in this transformation has been carried out. According to our proposed mechanism, only 1 equiv. of organolithium reagent will be required for the transformation of fully alkylated sulfoxides into glycals, whereas 2,3-isopropylidene-protected sulfoxides will require a second equivalent of organolithium reagent to react with the acetone liberated in the process (see A. Klemer, G. Rodemeyer, Chem. Ber. 1974, 107, 2612-2614, However, we have observed that the use of 3 equiv. of organolithium reagent works reasonably well in all instances. Sulfoxide 16, bearing a free hydroxy group, was treated with 4 equiv. of nBuLi for its transformation into glycal 19 see Experimental Section
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