Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols

[Image: see text] Axially chiral 2-(2-(trifluoromethyl)-1H-benzo[d]imidazole-1-yl)benzoic acid (TBBA) was used as a chiral derivatizing agent to evaluate the limits of absolute configuration assignment for β-chiral aminoalcohols. Seven Boc-aminoalcohols and eight variously N-substituted (S)-phenylgl...

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Autores principales: Kriegelstein, Michal, Profous, David, Přibylka, Adam, Lyčka, Antonín, Cankař, Petr
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9025982/
https://www.ncbi.nlm.nih.gov/pubmed/35474810
http://dx.doi.org/10.1021/acsomega.1c07234
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author Kriegelstein, Michal
Profous, David
Přibylka, Adam
Lyčka, Antonín
Cankař, Petr
author_facet Kriegelstein, Michal
Profous, David
Přibylka, Adam
Lyčka, Antonín
Cankař, Petr
author_sort Kriegelstein, Michal
collection PubMed
description [Image: see text] Axially chiral 2-(2-(trifluoromethyl)-1H-benzo[d]imidazole-1-yl)benzoic acid (TBBA) was used as a chiral derivatizing agent to evaluate the limits of absolute configuration assignment for β-chiral aminoalcohols. Seven Boc-aminoalcohols and eight variously N-substituted (S)-phenylglycinols were prepared, and their TBBA esters were analyzed by NMR spectroscopy. Diverse substitution at the β-position was employed to demonstrate the effect of structure on the general conformational model and reliability of the absolute configuration assignment. It was concluded that hydrogen bond formation and steric hindrance were the main factors affecting the correct assignment for Boc-aminoalcohols.
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spelling pubmed-90259822022-04-25 Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols Kriegelstein, Michal Profous, David Přibylka, Adam Lyčka, Antonín Cankař, Petr ACS Omega [Image: see text] Axially chiral 2-(2-(trifluoromethyl)-1H-benzo[d]imidazole-1-yl)benzoic acid (TBBA) was used as a chiral derivatizing agent to evaluate the limits of absolute configuration assignment for β-chiral aminoalcohols. Seven Boc-aminoalcohols and eight variously N-substituted (S)-phenylglycinols were prepared, and their TBBA esters were analyzed by NMR spectroscopy. Diverse substitution at the β-position was employed to demonstrate the effect of structure on the general conformational model and reliability of the absolute configuration assignment. It was concluded that hydrogen bond formation and steric hindrance were the main factors affecting the correct assignment for Boc-aminoalcohols. American Chemical Society 2022-04-04 /pmc/articles/PMC9025982/ /pubmed/35474810 http://dx.doi.org/10.1021/acsomega.1c07234 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kriegelstein, Michal
Profous, David
Přibylka, Adam
Lyčka, Antonín
Cankař, Petr
Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
title Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
title_full Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
title_fullStr Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
title_full_unstemmed Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
title_short Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
title_sort limitations of trifluoromethylbenzoimidazolylbenzoic acid as a chiral derivatizing agent to assign absolute configuration for β-chiral aminoalcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9025982/
https://www.ncbi.nlm.nih.gov/pubmed/35474810
http://dx.doi.org/10.1021/acsomega.1c07234
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