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  • Title: Chiral resolution through precipitation of diastereomeric capsules in the form of 2:1 beta-cyclodextrin-guest complexes.
    Author: Bakirci H, Nau WM.
    Journal: J Org Chem; 2005 May 27; 70(11):4506-9. PubMed ID: 15903333.
    Abstract:
    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.
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