A catalytic asymmetric aldol reaction proceeding via a chiral palladium(II)) enolate is described. The novel chiral diaquo palladium(II) complexes of (R)-BINAP (9a), and (R)-Tol-BINAP (9b) were prepared in good yield, and their structures were determined by X-ray crystallography. These air- and moisture-stable complexes were found to be excellent catalysts for the asymmetric aldol reaction, and up to 89% ee of asymmetric induction was achieved using these catalysts.