| Abstract
| - For the first time, achiral cucurbiturils (CBs) were endowed with significant enantiomeric anddistereomeric discrimination by incorporating a strong chiral binder. Calorimetric, nuclear magnetic, light-scattering, and mass spectral studies revealed that (S)-2-methylbutylamine (as a strong binder) can bediscriminated by two enantiomeric supramolecular hosts, composed of CB[6] and (R)- or (S)-2-methylpiperazine, with an unprecedented 95% enantioselectivity in aqueous NaCl solution. This is the highestenantioselectivity ever reported for a supramolecular system derived from an achiral host. Similarly, CB[7],with a larger cavity, exhibited diastereoselectivities up to 8 times higher for diastereomeric dipeptides, asdemonstrated for l-Phe-l-Leu-NH3+ versus l-Phe-d-Leu-NH3+.
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