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A new, enantioselective synthesis of Orlistat suitable for large-scale production is described, wherein the first enantiomerically pure intermediate methyl (R)-3-hydroxy-tetradecanoate is prepared via asymmetric hydrogenation of methyl 3-oxotetradecanoate. The relevant criteria associated with the application of the asymmetric hydrogenation technology are addressed, such as the activity, the selectivity and the availability of the catalyst as well as the quality of the hydrogenation substrate and the hydrogen gas.