The diastereoselective aldol reaction of tributyltin enolate of cyclohexanone with benzaldehyde was studied in the presence of a catalytic amount of various metal triflates. The highest anti selectivity was observed with Pd(OTf)2, while Zn(OTf)2 in THF showed moderate syn selectivity. The use of (S,S)-iPr-pybox 3 ⋅ Cu(OTf)2 complex as a catalyst preferentially produced the optically active syn aldol adduct with 84% ee.