Recognition of Planar Chirality by Cyclodextrins

Recognition of planar chirality of 14-hydroxy-12-oxabicyclo[9.2.2]pentadecane-1(14),11(15)-diene-1,13-dione (C8) and 16hydroxy-14-oxabicyclo[11.2.2]heptadecane-1(16),13(17)-diene-2,15-dione (C10) by native and O-methylated cyclodextrins has been studied by NMR spectroscopy. The cyclodextrins prefer the (R)-enantiomers of C8 and C10, which might well fit with asymmetrically twisted cavities of cyclodextrins.