STEREOISOMERIC FLAVOR COMPOUNDS .52. SEPARATION AND STRUCTURE ELUCIDATION OF THE FURANOID LINALOOL OXIDE STEREOISOMERS USING CHIROSPECIFIC CAPILLARY GAS-CHROMATOGRAPHY AND NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPY

Using heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin as the chiral stationary phase in capillary gas chromatography, the direct stereodifferentiation of the four furanoid linalool oxide stereoisomers has been achieved. The structure elucidation of the two geometrical isomers by H-1 NMR spectroscopy (including intramolecular nuclear Overhauser effects of the separated diastereomers) is now reported. The elution order of the optical isomers is ascertained by synthesis and chromatography of the (2R)-configured diastereomers, starting from (R)-linalool.