In summary, we described in this study a new concept of simultaneous production of enantiomers in association with a physical separation, starting from a racemic mixture. The principle relies on a compartmentalized parallel kinetic resolution (CPKR) combining enantioselective catalysis and selective permeability of membrane. The racemic substrates with a low polarity can cross the membrane while each enantiomeric product is sequestrated in one compartment due to its higher polarity. This concept was successfully established with Jacobsen's HKR of terminal epoxide. Chirality of both substrate and product was used as a probe to evaluate their diffusion rates through the membrane in absence of concentration gradient between the two compartments. From this unprecedented study, we were able to evaluate the selectivity of the membrane required for the feasibility of such PKR process. Due to the prevalence of polarity changes between substrates and products in organic transformations, numerous applications of this process can be expected with high academic and industrial potential.