Coordination of a chiral substrate to (meso-salen)cobalt(II) nitrate and subsequent oxidation generates a Co(III) complex exhibiting a strong chiroptical readout that is attributed to spontaneous substrate-to-ligand chirality imprinting. The characteristic circular dichroism (CD) response of the (salen)cobalt complex can be used for enantiomeric analysis of a variety of chiral substrates based on a simple CD measurement at low concentration and without additional purification steps. This chirality sensing approach has potential for high-throughput enantiomeric excess (ee) screening applications and minimizes solvent waste production.