Enantiopure aziridin-2-yl methanols 3 – 7 are used as highly effective sensors for enantiodiscrimination of α-racemic carboxylic acids containing tertiary or quaternary stereogenic centers. A linear correlation between theoretical and observed % ee values for CSA- 3 and enantiomerically enriched samples of mandelic acid has been observed, indicating the possible application of these compounds in the ee determination. The free NH and OH groups in 3 – 7 ensure good recognition.

A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy.