Enantioselective Solid-Liquid Extraction of Native Saccharides with Chiral BINOL-Based Pyridine-Phenol Type Macrocycles

Organic Letters
Yuki OhishiMasahiko Inouye

Abstract

A chiral 1,1'-bi-2-naphthol (BINOL)-containing pyridine-acetylene-phenol macrocycle and a pyridine-BINOL alternating macrocycle were developed for enantioselective recognition of saccharides. In solid-liquid extraction of native saccharides, these macrocycles selectively extracted one enantiomer from each of a racemic mixture of d/l-fructose, d/l-glucose, and d/l-mannose into a lipophilic solvent. This is the first example in which native saccharides, especially such important hexoses, were enantioselectively extracted with artificial host molecules.

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