The deoxygenation of sulfoxide mediated by the Ph3P/Lewis acid combination and the application to the kinetic resolution of racemic phosphines using optically active sulfoxide

It was found that the combination of Ph3P/TiCl4 was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in good yield (up to 97%) under mild conditions. This method was applied to the reaction between racemic phosphines and (R)-methyl p-tolyl sulfoxide, and it was found that the kinetic resolution was achieved in moderate selectivities. (c) 2005 Elsevier Ltd. All rights reserved.