Hydrogenation of the prochiral diketone, 1,2-indanedione was for the first time investigated using cinchonidine-modified Pt/Al2O3 as a catalyst. The influence of the reaction parameters on catalyst activity, regio- and enantioselectivity was studied revealing fully regioselective hydrogenation of the C(2)-keto group. Enantioselectivities of the (R)- versus (S)-2-hydroxy-1-indanone varied from low to moderate in favor of the (R)-enantiomer. A systematic study of enantioselective hydrogenation of 1,2-indanedione - a new substrate for chirally modified heterogeneous catalysts - over cinchonidine modified Pt/Al2O3 is presented. The influence of the reaction parameters on activity, regio- and enantioselectivity was studied. [GRAPHICS]