An ingenious method for the determination of the relative and absolute configurations of compounds containing aryl-glycerol fragments by H NMR spectroscopy.

A concise method was established to determine the relative and absolute configurations of aryl-glycerols that depend on the chemical shift differences (Δ) of the diastereotopic methylene protons (H-3) by H NMR spectroscopy. When using DMSO- as the preferred solvent, the configuration corresponded to a larger Δ value (>0.15 ppm), whereas the configuration (<0.07 ppm) corresponded to a smaller value. Furthermore, the absolute configurations were determined with the aid of a simple acylation reaction through camphanoyl chloride. In the enantiomers, the Δ value of the 1,2 configuration was <0.15 ppm, and that of the 1,2 configuration was >0.20 ppm. In the enantiomers, the Δ value of 1,2 was >0.09 ppm, and that of 1,2 was <0.05 ppm. Remarkably, this empirical rule is invalid in CDCl. In addition, this method was also verified by a quantum H NMR calculation.