Abstract The reduction of racemic RPhMeSiCCl 2 CH 3 systems (R= cyclohexyl, isopropyl, t- butyl and 2-mesityl) to the diastereomeric RPhMeSiCHClCH 3 with tributyltin hydride was used as a probe into the potential of the RPhMeSi group to induce asymmetry at an α position. Favorable results were obtained for R= mesityl.