Highly efficient NMR enantiodiscrimination of 1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane, a chiral degradation product of sevoflurane, by heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin

The molecular basis of the efficient enantiodiscrimination of 1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane, a chiral degradation product of the inhalation anaesthetic sevoflurane, using heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin as chiral selector, has been investigated by NMR spectroscopy. An interaction mechanism is proposed, which highlights the role of the functional groups on the β-cyclodextrin rims in addition to a partial molecular inclusion.

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Heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrinC112H196O49Si7[α]D33=+86.9 (c 1.0, CHCl3)Source of chirality: β-cyclodextrin