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DOI: 10.1055/s-0041-1737992
Methods for Determination of Absolute Configurations of Chiral Diols by THENA Ester and NMR Shift Difference
Financial support from Mahidol University and the Thailand Research Fund (Grant BRG5480020), the Royal Golden Jubilee Ph.D. Programme (Grant PHD/0032/2554) to K.D. and T.T., the Center of Excellence for Innovation in Chemistry (PERCH-CIC), and the Development of Pharmaceuticals from Bioresources and Its Management (NRU) for J.S. are gratefully acknowledged.
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Abstract
Determination of the absolute configuration of chiral secondary diols by chiral derivatizing agent (CDA) and NMR shift difference is of great challenge due to the complication from the interference of the aromatic anisotropic shielding effect of the two CDAs in close proximity. In this work, tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid (THENA) was introduced as an alternative CDA for diols to overcome such complexity. Since the deshielding effect of THENA is weaker than the shielding effect of other CDAs, THENA would allow the direct analysis of the chemical shift difference in determining the absolute configuration of the chiral diols. In addition, an analytical method based on Riguera’s model could also be used to confirm the assignment. With a good agreement between the assigned configuration based on both analytical models, the absolute configuration of the chiral diols could be assigned with reliability.
Key words
absolute configuration - chiral derivatizing agent - diols - NMR shift difference - natural products - stereochemistry - THENASupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737992.
- Supporting Information
Publication History
Received: 01 February 2022
Accepted after revision: 09 March 2022
Article published online:
06 May 2022
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References and Notes
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