The state of the art for the heterogeneous enantioselective hydrogenation of alpha-ketoesters using cinchona modified Pt catalysts and related systems is reviewed. The effect of the following elements of the catalytic system are well known : Catalyst. Supported Pt catalysts with relatively low dispersion (particle diameter >2 nm) are preferred for the hydrogenation of alpha-ketoacid derivatives, Pd catalysts for functionalized olefins. Most support materials are suitable. Substrate. The reacting function is preferentially a ketone or a C=C bond, a carbonyl group in alpha-position is necessary for good optical yields. Modified The minimal requirements for an efficient modifier for the hydrogenation of alpha-ketoesters is the presence of a basic nitrogen atom close to one or more stereogenic centers and connected to an extended aromatic system (preferentially quinolyl or naphthyl). The presence of an alcohol or ether in beta-position to the basic nitrogen often gives better enantioselectivities. Solvent. Solvents with a dielectric constant between 2 and 10 give best selectivities for beta-ketoesters with best e.e.’s in acetic acid. For the hydrogenation of substrates with a free acid function aqueous polar solvents are preferred. The highest optical yields for the different substrate types : 95% e.e. for alpha-ketoesters, 85% for alpha-ketoacids and 70% for alpha,beta-unsaturated acids. Practical problems for the use of the catalytic system are low e.e.’s at the start of the reaction, the instability of the modifier and some side reactions as well as the purity of the ethyl pyruvate. Mechanistic investigations have established interactions between substrate and modifier in solution and adsorption of the ethyl pyruvate and cinchonidine on the catalyst. The dependence of rate and e.e. on catalyst, cinchonidine, ethyl pyruvate and hydrogen concentration-has been established for ethyl pyruvate hydrogenation using Pt/Al2O3-cinchona, A Langmuir-Hinshelwood scheme is well suited for explaining the observed kinetic results. Based on the kinetic results, the effect of modifier and substrate structure, and molecular modeling studies, the following mechanistic model has been developed. On the unmodified catalyst, the alpha-ketoester and hydrogen are reversibly adsorbed and the addition of the first hydrogen atom is rate determining. A modified active site is formed by adsorption of one cinchona molecule. It is postulated that a protonated adsorbed modifier interacts with the alpha-ketoester and forms a stabilized half hydrogenated intermediate. The rate determining step for the preferred enantiomer is the addition of the second hydrogen, The rate acceleration and the enantiodiscrimination is therefore due to the preferential stabilization of one of the two diastereomeric intermediates. Alternative mechanisms are discussed but considered to be less satisfying.