Authors: Wulff G
, Stellbrink H
On the chemistry of binding-sites .7. Enantioselective binding using chiral boronic acids.
Publication date: 1990
Journal: Recueil Des Travaux Chimiques Des Pays-Bas-Journal Of The Royal Netherlands Chemical Society
Abstract: For the construction of chiral binding sites in chromatography, various phenylboronic acids have been prepared as model substances carrying, in the ortho (3a-d) or ortho,' position (4a-d), optically active side-groups containing basic nitrogen atoms. The compound carrying two prolyl residues shows the highest selectivity in chiral recognition of racemic diols (separation factor ~ between 1.70-2.25). Separation occurs via the formation of a cyclic boronic diester of the diol. The thermodynamic properties of this esterification reaction are well suited to chromatography and furthermore the reaction seems to be adequately rapid
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