Among the numerous stereodiscrimination methods, nuclear magnetic resonance (NMR) spectroscopy continues to be one of the leading tools for determining the enantiomeric purity of chiral molecules. However, enantiomers cannot be distinguished in an achiral environment as NMR active nuclei are isochronous. Usually, some external source of chirality is introduced in the form of a covalently bonding chiral derivatization agent (CDA), a non-covalently interacting solvating agent (CSA), or even self-induced recognition of enantiomers (SIRE) to convert the enantiomeric systems into diastereomeric ones. Recently, a new type of NMR spectroscopic detection of enantiomeric excess (e.e.) using prochiral solvating agents (pro-CSA) was introduced by Hill and co-workers. In principle, in the event of attractive noncovalent physicochemical interactions, the chiral information of a guest can be transferred to an achiral host and detected as the splitting of the NMR signals. The key example of pro-CSA, N,N'-disubstituted oxoporphyrinogen (Bz2oxP) exhibits a linear response between the e.e. value and the magnitude of -proton splitting (∆) in H NMR (Figure ). Due to N-alkylation of the Bz2oxP core, the system cannot be protonated and hence suffers serious sensitivity issues compared to unmodified oxP. However, the inevitable prototropic tautomerism and macrocyclic inversions obstruct the potential applications of oxP as a pro-CSA. Porphyrins, as prospective pro-CSA candidates for e.e. detection, have also been investigated. While 5,10,15,20-tetraphenylporphyrin (TPP) is not affected by the disadvantageous tautomeric processes, as opposed to oxP, the necessary use of depressed temperatures for the e.e. detection limits the analysis to explicit solvents with a low freezing point (e.g. CDCl3) and analyte solubility during the screening (e.g. precipitation).