Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR

A novel and efficient method for distinguishing between chiral diols and diphenols has been established through the use of 19F NMR spectroscopy. Central to this system's efficacy is a chiral amine, strategically modified with a CF3 group. This amine reacts in-situ with 2-formylphenylboronic acid to create a chiral 19F-labeled probe. This probe demonstrates discriminatory capabilities by interacting with hydroxy-containing analytes to form boronic esters. These esters produce distinct 19F NMR signals that vary according to their stereoconfiguration, facilitating accurate chiral differentiation. The method's resolution capacity was demonstrated by successfully identifying 12 distinct chiral analytes (six pairs of enantiomers) in complex mixtures, highlighting its extensive potential in diverse chiral analysis applications.