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Application of NMR Spectroscopy for the Detection of Equilibrating E–Z Diastereomers
[Image: see text] Conjugation can lower the energy barrier for unsaturated C–C bond rotations, resulting in a mixture of equilibrating diastereomers at room temperature. Therefore, methods claiming diastereoselective synthesis of conjugated double bonds often require proof that the observed diastere...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7528312/ https://www.ncbi.nlm.nih.gov/pubmed/33015503 http://dx.doi.org/10.1021/acsomega.0c03554 |
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author | Hussaini, Syed Raziullah Kuta, Adama Pal, Arpan Wang, Zhiguo Eastman, Margaret A. Duran, Ramon |
author_facet | Hussaini, Syed Raziullah Kuta, Adama Pal, Arpan Wang, Zhiguo Eastman, Margaret A. Duran, Ramon |
author_sort | Hussaini, Syed Raziullah |
collection | PubMed |
description | [Image: see text] Conjugation can lower the energy barrier for unsaturated C–C bond rotations, resulting in a mixture of equilibrating diastereomers at room temperature. Therefore, methods claiming diastereoselective synthesis of conjugated double bonds often require proof that the observed diastereomeric ratio is not because of the diastereomeric equilibration of the product. Variable-temperature (VT) NMR experiments are commonly used to distinguish between the two possibilities. However, the VT technique requires accessories for the NMR spectrometer and more setup time. Here, we show that the rarely used application of 1-D and 2-D nuclear Overhauser effect spectroscopy experiments for the detection of the equilibrating diastereomers is a convenient alternative to the VT technique. |
format | Online Article Text |
id | pubmed-7528312 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-75283122020-10-02 Application of NMR Spectroscopy for the Detection of Equilibrating E–Z Diastereomers Hussaini, Syed Raziullah Kuta, Adama Pal, Arpan Wang, Zhiguo Eastman, Margaret A. Duran, Ramon ACS Omega [Image: see text] Conjugation can lower the energy barrier for unsaturated C–C bond rotations, resulting in a mixture of equilibrating diastereomers at room temperature. Therefore, methods claiming diastereoselective synthesis of conjugated double bonds often require proof that the observed diastereomeric ratio is not because of the diastereomeric equilibration of the product. Variable-temperature (VT) NMR experiments are commonly used to distinguish between the two possibilities. However, the VT technique requires accessories for the NMR spectrometer and more setup time. Here, we show that the rarely used application of 1-D and 2-D nuclear Overhauser effect spectroscopy experiments for the detection of the equilibrating diastereomers is a convenient alternative to the VT technique. American Chemical Society 2020-09-16 /pmc/articles/PMC7528312/ /pubmed/33015503 http://dx.doi.org/10.1021/acsomega.0c03554 Text en This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Hussaini, Syed Raziullah Kuta, Adama Pal, Arpan Wang, Zhiguo Eastman, Margaret A. Duran, Ramon Application of NMR Spectroscopy for the Detection of Equilibrating E–Z Diastereomers |
title | Application of NMR Spectroscopy for the Detection
of Equilibrating E–Z Diastereomers |
title_full | Application of NMR Spectroscopy for the Detection
of Equilibrating E–Z Diastereomers |
title_fullStr | Application of NMR Spectroscopy for the Detection
of Equilibrating E–Z Diastereomers |
title_full_unstemmed | Application of NMR Spectroscopy for the Detection
of Equilibrating E–Z Diastereomers |
title_short | Application of NMR Spectroscopy for the Detection
of Equilibrating E–Z Diastereomers |
title_sort | application of nmr spectroscopy for the detection
of equilibrating e–z diastereomers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7528312/ https://www.ncbi.nlm.nih.gov/pubmed/33015503 http://dx.doi.org/10.1021/acsomega.0c03554 |
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