The chemoenzymatic dynamic kinetic resolution of β-amino esters is established after detailed evaluation of metal-based heterogeneous catalysts for racemization and enzyme catalysts for kinetic resolution. Several heterogeneous palladium catalysts proved to be able to perform racemization of the model substrate, propyl β-phenylalaninate. The catalysts were characterized and their kinetics evaluated to eventually select two different but promising racemization catalysts. Relations were established between physical catalyst characteristics and the selectivities in the racemization and DKR reactions. By combining racemization with the kinetic resolution, an efficient DKR was realized with excellent enantioselectivity and yields for a significant scope of β-amino esters.