Ever since the first sorting of enantiomers by Louis Pasteur, crystallization has become a powerful method for isolating molecules of a desired handedness. Although in the past century many variations of this method have been developed, widespread use of chiral purification by crystallization is still hindered by one imperative: enantiomers need to sort themselves in separate enantiopure crystals (i.e. racemic conglomerates). Unfortunately, the overwhelming majority of enantiomeric mixtures crystallizes into thermodynamically favored racemic compounds (90- 95%), which hinders such separation techniques. We suggest that this thermodynamic limitation may be overcome by exploiting non-equilibrium conditions, in which crystallization rates - instead of thermodynamic stabilities alone - may determine which crystalline phase dominates. This opens the potential to exploit non-equilibrium conditions for favoring enantiopure crystals at the expense of stable racemic compounds. Motivated by these insights, we analyzed energy differences between racemates and their enantiopure counterparts (ΔGΦ) for two libraries of biorelevant target molecules with different chemical modifications. We found, surprisingly,a large and continuous distribution ofΔGΦ, in which similar chemical modifications are clustering. This enabled a directed evolutionary design strategy (i.e. iterative methodological library design) to discover systems with low ΔGΦ (< 0.5 kcal.mol-1), for which we demonstrate that the desired enantiomer can be isolated by preferential crystallization or deracemization under non-equilibrium conditions. Comparison with over a hundred previously reported racemic compounds suggests that the continuum of ΔGΦ of structurally related compounds offers much better odds for discovering kinetically stabilizable conglomerates (50-60%). Hence, both the evolutionary library design and exploitation of non-equilibrium open up many new opportunities for crystallization-based routes towards enantiopure molecules that are essential in our daily lives.