Chiral resolution through precipitation of diastereomeric capsules in the form of 2:1 beta-cyclodextrin-guest complexes.
Preferential precipitation of one enantiomer from a racemic mixture of a camphanate ester of 2,3-diazabicyclo[2.2.2]oct-2-ene was induced by the formation of diasteromeric 2:1 beta-cyclodextrin-guest complexes. The precipitate was enriched with the (-)-enantiomer and the supernatant solution with the (+)-form of a camphanate ester, which was quantitatively analyzed in terms of differential binding constants and intrinsic solubilities of the 2:1 complexes. The enantiomeric excess in the precipitate was determined as 30 +/- 3% by induced circular dichroism.
Bakirci
Hüseyin
H
School of Engineering and Science, International University Bremen, Campus Ring 1, 28759 Bremen, Germany. w.nau@iu-bremen.de
Nau
Werner M
WM
D002942:Circular Dichroism; D015394:Molecular Structure; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
D047392:beta-Cyclodextrins