Methods for Determination of Absolute Configurations of Chiral Diols by THENA Ester and NMR Shift Difference
Issued Date
2022-09-01
Resource Type
ISSN
09365214
eISSN
14372096
Scopus ID
2-s2.0-85132672275
Journal Title
Synlett
Volume
33
Issue
14
Start Page
1438
End Page
1442
Rights Holder(s)
SCOPUS
Bibliographic Citation
Synlett Vol.33 No.14 (2022) , 1438-1442
Suggested Citation
Dolsophon K., Soponpong J., Kornsakulkarn J., Thongpanchang C., Thongpanchang T. Methods for Determination of Absolute Configurations of Chiral Diols by THENA Ester and NMR Shift Difference. Synlett Vol.33 No.14 (2022) , 1438-1442. 1442. doi:10.1055/s-0041-1737992 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/84165
Title
Methods for Determination of Absolute Configurations of Chiral Diols by THENA Ester and NMR Shift Difference
Author's Affiliation
Other Contributor(s)
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.
