Regio-selective reduction of the C–C double bonds in α,β-unsaturated acyl 4-substituted oxazolidin-2-ones and oxazolidine-2-thiones

Selective saturation of the conjugated C–C double bonds in the title compounds was examined in a systematic way for the first time. Many established protocols effective for similar reduction of α,β-unsaturated ketones and esters in the literature were found to be inapplicable in the present context. The most satisfactory results were finally obtained using the DIBAL-H/MeLi/CuI/HMPA/THF conditions.