Optically pure 2-(quinolin-8-yloxy)cyclohexan-1-ol as a practical agent for molecular recognition by NMR and fluorescence spectroscopy

Abstract

Optically pure 2-(quinolin-8-yloxy)cyclohexan-1-ol 1, obtained via simple chemical and bio-catalytic steps, was used as a chiral solvating agent for molecular recognition of the enantiomers of acids. The discrimination of isomers was detected by NMR or fluorescence spectroscopy. Isomers of α-substituted carboxylic acids, phosphoric acids, unprotected amino acids and dipeptides were efficiently detected, while the method can be used for quantitative determination for practical applications. Analysis of the crystal of (R,R)-1 (R)-mandelic acid established a three point supramolecular interaction.