4.7 Article

l-Proline, a resolution agent able to target both enantiomers of mandelic acid: an exciting case of stoichiometry controlled chiral resolution

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 61, Pages 8560-8563

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc02942a

Keywords

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Funding

  1. China Scholarship Council (CSC) - FNRS PDR grant [T.0149.19 -T.262.20]

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In this study, a significant development in chiral resolution is presented. By varying the stoichiometry, both R- and S-enantiomers of mandelic acid were successfully separated from a racemic mixture using l-proline as a resolving agent. This specific feature is achieved through the existence of stoichiometrically diverse cocrystal systems between R- and S-mandelic acid and l-proline.
We present a thought-provoking development in chiral resolution. Using a resolving agent of a given handedness, l-proline, we show that both R- and S-enantiomers of mandelic acid can be resolved from a racemic mixture simply by varying the stoichiometry. We are the first to report this specific feature, achieved by the existence of stoichiometrically diverse cocrystal systems between R- and S-mandelic acid and l-proline.

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