Substrate specificity of the kinetic resolution of sulfides by enantioselective sulfoxide formation

Article abstract of DOI:10.1016/S0957-4166(97)00205-X

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.