SYNTHESIS OF (4S,5R)-(-)-4-METHYL-5-PHENYLOXAZOLIDINE-2-SELONE - A CHIRAL AUXILIARY REAGENT CAPABLE OF DETECTING THE ENANTIOMERS OF (R,S)-LIPOIC ACID BY SE-77 NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPY

(4S,5R)-(-)-4-Methyl-5-phenyloxazolidine-2-selone was constructed in 5 steps on the 10-gram scale. Se-77 NMR spectroscropic studies revealed that this selone served as a remarkably sensitive chiral auxiliary agent which readily distinguished the selone-coupled (R,S)-lipoic acid (DELTA-delta 0.119 ppm), even though its chiral centre was separated by 8 bonds from the observed nucleus.