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

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F22%3A50019290" target="_blank" >RIV/62690094:18470/22:50019290 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acsomega.1c07234" target="_blank" >https://pubs.acs.org/doi/10.1021/acsomega.1c07234</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acsomega.1c07234" target="_blank" >10.1021/acsomega.1c07234</a>

Result language
angličtina
Original language name
Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for beta-Chiral Aminoalcohols
Original language description
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 beta-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 beta-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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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