NMR DIFFERENTIATION OF ENANTIOMERIC (+)-ALPHA-PINENE AND (-)-ALPHA-PINENE VIA COMPLEXATION WITH CYCLODEXTRINS IN WATER

(+)- and (-)-alpha-Pinene form diastereoisomeric complexes with alpha-, 2,3,6-tri-O-methyl-alpha-, 2,3,6-tri-0-methyl-beta- and 2,3,6-tri-O-acetyl-beta-cyclodextrin which are distinguishable in H-1 and C-13 NMR spectra, the alpha-pinene protons obeying the slow exchange condition during the complexation process; utilization of cyclodextrins as chiral shift reagents for molecules lacking polar groups is consequently proposed.