Substrate Specificity of the Kinetic Resolution of Sulfides by Enantioselective Sulfoxide Formation.

Abstract The kinetic resolution of tazofelone ( 1 ) has been reported. The resolution of this sulfide was accomplished via enantioselective sulfoxide formation with tert -Bu hydroperoxide in the presence of a chiral tartrate/titanium complex. The resolution was performed on analogues of compound 1 in order to explore the substrate specificity of the kinetic resolution. These experiments have shown that the success of the enantioselective oxidation of this sulfide by tert -Bu hydroperoxide is greatly influenced by the nature of the neighboring amide functionality.