4.7 Article

A [5]HELOL analogue that senses remote chirality in alcohols, phenols, amines, and carboxylic acids

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 21, Pages 8497-8502

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo0512913

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A route is developed to a structural analogue of [5]HELOL, a previously reported helically grooved sensor of remote chirality. It gives the material enantiomerically pure and in multigram quantities. The enantiomers of alcohols, phenols, amines, and carboxylic acids, even when their centers of chirality are remote from any functional groups, can be differentiated by P-31 NMR spectroscopic analyses of their reaction products with the chlorophosphite of this material.

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