Kinetics and modeling of 1-phenyl-1,2-propanedione hydrogenation over cinchonidine-modified Pt/Al2O3 catalyst is reported. Hydrogenation experiments carried out in a pressurized autoclave (288 K, 1.2-6.5 bar hydrogen) revealed interesting kinetic effects which inspired the model development. The enantioselectivity towards the (R)-configuration, as well as the reaction rate and regioselectivity, depended on the modifier concentration having a maximum. The enantio- and regioselective effects were explained by the kinetic model, which assumes different number of sites for adsorption of the carbonyl groups of the 1-phenyl-1,2-propanedione as well as for the cinchonidine adsorbed in flat and tilted modes. The number of adsorption sites needed for the different species were obtained from molecular considerations and the hydrogenation rate constants were determined along with the adsorption parameters by non-linear regression analysis. A comparison of model predictions with experimental data revealed that the model accounts for the kinetic regularities.