Issue 14, 2021, Issue in Progress

An ingenious method for the determination of the relative and absolute configurations of compounds containing aryl-glycerol fragments by 1H NMR spectroscopy

Abstract

A concise method was established to determine the relative and absolute configurations of aryl-glycerols that depend on the chemical shift differences (Δδ) of the diastereotopic methylene protons (H-3) by 1H NMR spectroscopy. When using DMSO-d6 as the preferred solvent, the threo configuration corresponded to a larger ΔδH3a–H3b value (>0.15 ppm), whereas the erythro configuration (<0.07 ppm) corresponded to a smaller value. Furthermore, the absolute configurations were determined with the aid of a simple acylation reaction through camphanoyl chloride. In the threo enantiomers, the Δδ value of the 1R,2R configuration was <0.15 ppm, and that of the 1S,2S configuration was >0.20 ppm. In the erythro enantiomers, the Δδ value of 1R,2S was >0.09 ppm, and that of 1S,2R was <0.05 ppm. Remarkably, this empirical rule is invalid in CDCl3. In addition, this method was also verified by a quantum 1H NMR calculation.

Graphical abstract: An ingenious method for the determination of the relative and absolute configurations of compounds containing aryl-glycerol fragments by 1H NMR spectroscopy

Supplementary files

Article information

Article type
Paper
Submitted
16 Nov 2020
Accepted
11 Feb 2021
First published
19 Feb 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 8107-8116

An ingenious method for the determination of the relative and absolute configurations of compounds containing aryl-glycerol fragments by 1H NMR spectroscopy

X. Zhang, K. Lu, H. Yan, Z. Feng, Y. Yang, J. Jiang and P. Zhang, RSC Adv., 2021, 11, 8107 DOI: 10.1039/D0RA09712H

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