Dense enantioselective membranes can distinguish between two enantiomers by different mechanisms. At this moment, it is not clear which mechanism provides the best membranes for large-scale enantiomer separations. Therefore, we studied the design criteria for permeation-selective membranes combining literature data, experiments and model calculations. Literature data on dense permeation-selective membranes for enantiomer separation show that these membranes could be divided into two different classes: diffusion selective and sorption selective. Reviewing the literature on diffusion-selective membranes shows that these membranes have one main disadvantage: the inverse proportionality relation between the permeability and selectivity This disadvantage is absent for sorption-selective membranes. As a model system, the diffusion of phenylalanine through a packed bed of polypropylene beads coated with N-dodecyl-L-hydroxyproline:Cu(II) was studied. The experiments showed that the material could selectively adsorb phenylalanine (Phe) with a selectivity (D/L) of 1.25. However, no permeation selectivity could be detected, With a dual sorption model these results could be interpreted. These model calculations showed that the permeation selectivity only approaches the intrinsic selectivity of the selector if the selectively adsorbed population is mobile and the non-selective permeation is minimized. Therefore, to our opinion more emphasis should be put on the development of sorption selective membranes.