Separation-free Enantiodifferentiation with Chromatogram-like Output

Chromatographic-based approaches are most widely used for the analysis of enantiomers. Unambiguous results are achieved through the visualization of each enantiomer, while the separation process is often time consuming. By endowing 19F probes with suitable dynamic recognition properties, we develop here a detection scheme that produces chromatogram-like output in the analysis of enantiomeric mixtures without separation. A wide range of chiral compounds, including alcohols, ethers, amides, carbamates, oxazolidinones, sulfoxides, and sulfoximines, are successfully resolved, and the simultaneous enantiodifferentiation of different classes of chiral compounds is achieved. The method is also amenable for the determination of the enantiopurity of crude reaction products and the assignment of absolute configurations. The potential utility in high-throughput screening is demonstrated by the analysis of 24 nonracemic samples in 30 min with an NMR spectrometer equipped with an autosampler.