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The optically pure compounds have supreme importance in pharmaceuticals, agrochemicals, fine chemicals, and biochemical research as enantiomers express themselves differently in biological systems. Presently optically active compounds in their high optical purity are mainly obtained through (i) asymmetric catalysis, (ii) enantiomer separation with the use of various chemical/analytical techniques. Nowadays, the separation of chirally pure compounds at qualitative and quantitative scale using different chromatographic techniques with chiral stationary phases (CSPs) and enantiomer self-disproportionation (ESD) has become a vital requirement. This is because CSPs and ESD are the most powerful and practical tool for making chirally pure compounds when both the form of isomers are required. The main objective of our research is to investigate a practical, reusable, rapid, and efficient process among CSP and ESD based chromatography, as selective separation is concern. Subsequently, wehave investigated the application of these CSPs as recyclable heterogeneous catalysts for asymmetric nitroaldol reaction to afford chiral nitroalcohols in good to excellent yields and enantioselectivity.