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

A novel and efficient method for distinguishing between chiral diols and diphenols has been established through the use of F NMR spectroscopy. Central to this system's efficacy is a chiral amine, strategically modified with a CF group. This amine reacts with 2-formylphenylboronic acid to create a chiral F-labeled probe. This probe demonstrates discriminatory capabilities by interacting with hydroxy-containing analytes to form boronic esters. These esters produce distinct F 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.