Issue 10, 2014

A versatile ternary ionic complex for chiral discrimination of molecules with diverse functionalities using 1H NMR

Abstract

This study reports a simple, efficient and versatile protocol developed for NMR spectroscopic enantiodiscrimination of molecules containing diverse functional groups, such as amino alcohols, secondary alcohols, cyanohydrins, oxazolidones, diols, thiones and epoxides, using a phosphorous based three component mixture. The simple mixing and shaking of enantiopure 1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (BNPA), 4-(dimethylamino)pyridine (DMAP) and a chiral analyte in the solvent CDCl3 served as a chiral solvating agent and resulted in well dispersed peaks for each enantiomer in the 1H NMR spectrum. Discrimination could be achieved not only for the proton at the chiral centre, but also for multiple proton sites. The devised approach also permitted the precise measurement of the enantiomeric excess (ee).

Graphical abstract: A versatile ternary ionic complex for chiral discrimination of molecules with diverse functionalities using 1H NMR

Supplementary files

Article information

Article type
Paper
Submitted
20 Mar 2014
Accepted
25 Jun 2014
First published
26 Jun 2014

New J. Chem., 2014,38, 4908-4912

Author version available

A versatile ternary ionic complex for chiral discrimination of molecules with diverse functionalities using 1H NMR

I. Pal, S. R. Chaudhari and N. Suryaprakash, New J. Chem., 2014, 38, 4908 DOI: 10.1039/C4NJ00417E

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