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1 2023

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Proces samo-dysproporcjowania enancjomerów podczas chromatografii kolumnowej

Wzorek Alicja, Kwiatkowska Magdalena, Urbaniak Mariusz, Gawdzik Barbara

Wiadomości Chemiczne

2023

[Z] 77, 5-6

425--448

The review is devoted to self-disproportionation of enantiomers (SDE) phenomenon which has been observed for many different classes of chiral organic compounds. The SDE phenomenon occurs when the fractionation of an enantioenriched sample due the application of a physicochemical process under achiral conditions results in the variation of the proportion of the enantiomers present across the fractions, though the overall composition in terms of the sample ee remains unchanged. The SDE process can be considered in terms of separating the excess enantiomer from the racemate. The basic terminology related to SDE was described. The formation of the SDE under chromatographic conditions is the result of an association process occurring in a solution of a chiral, non-racemic compound. Information on preferred interactions leading to homo-/heterochiral supramolecules can be provided by quantum chemical calculations, NMR spectroscopy and comparison of crystal structures of the racemic and enantiomeric crystals. Several examples of the chromatographic experiments with different classes of compounds were given in two purposes 1) to highlight the possibility of application SDE during column chromatography as the method for enantiopurification of the chiral, non-racemic compounds; 2) to demonstrate that a standard workup (chromatographic purification, evaporation) can alter the stereochemical outcome of asymmetric reactions.