Issue 1, 2016

Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents

Abstract

Enantiopure diphenylprolinols were synthesized from a commercially available starting material. The utility of 1H NMR spectroscopy for the differentiation of enantiomers using these chiral compounds as CSAs is stated, and their capacity acting as receptors for various carboxylic acids via hydrogen bonding is exploited. A linear relationship has been observed between the experimental and observed values of ee indicating the possible use of these compounds for quick and reliable analysis of enantiomerically enriched samples of various mandelic acids. From the experiments performed a preliminary conclusion indicated that the diphenylprolinol 1b with the free NH and OH is most effective in the chiral discrimination of carboxylic acids in 1H NMR.

Graphical abstract: Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents

Supplementary files

Article information

Article type
Research Article
Submitted
23 Aug 2015
Accepted
25 Nov 2015
First published
26 Nov 2015

Org. Chem. Front., 2016,3, 96-102

Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents

G. Li, J. Cao, W. Zong, X. Lei and R. Tan, Org. Chem. Front., 2016, 3, 96 DOI: 10.1039/C5QO00264H

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