Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent

A new optically active BINOL-amino alcohol has been designed and synthesized in a good yield and applied as chiral nuclear magnetic resonance (NMR) solvating agent for enantioselective recognition. Analysis by (1)H NMR spectroscopy demonstrated that it has excellent enantiodifferentiation properties...

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Autores principales: Li, Gaowei, Ma, Minshan, Wang, Guifang, Wang, Xiaojuan, Lei, Xinxiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7213237/
https://www.ncbi.nlm.nih.gov/pubmed/32432082
http://dx.doi.org/10.3389/fchem.2020.00336
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author Li, Gaowei
Ma, Minshan
Wang, Guifang
Wang, Xiaojuan
Lei, Xinxiang
author_facet Li, Gaowei
Ma, Minshan
Wang, Guifang
Wang, Xiaojuan
Lei, Xinxiang
author_sort Li, Gaowei
collection PubMed
description A new optically active BINOL-amino alcohol has been designed and synthesized in a good yield and applied as chiral nuclear magnetic resonance (NMR) solvating agent for enantioselective recognition. Analysis by (1)H NMR spectroscopy demonstrated that it has excellent enantiodifferentiation properties toward carboxylic acids and non-steroidal anti-inflammatory drugs (14 examples). The non-equivalent chemical shifts (up to 0.641 ppm) of various mandelic acids were evaluated by the reliable peak of well-resolved (1)H NMR signals. In addition, enantiomeric excesses of the ortho-chloro-mandelic acid with different enantiomeric ratio were calculated based on integration of proton well-separated splitting signals.
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spelling pubmed-72132372020-05-19 Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent Li, Gaowei Ma, Minshan Wang, Guifang Wang, Xiaojuan Lei, Xinxiang Front Chem Chemistry A new optically active BINOL-amino alcohol has been designed and synthesized in a good yield and applied as chiral nuclear magnetic resonance (NMR) solvating agent for enantioselective recognition. Analysis by (1)H NMR spectroscopy demonstrated that it has excellent enantiodifferentiation properties toward carboxylic acids and non-steroidal anti-inflammatory drugs (14 examples). The non-equivalent chemical shifts (up to 0.641 ppm) of various mandelic acids were evaluated by the reliable peak of well-resolved (1)H NMR signals. In addition, enantiomeric excesses of the ortho-chloro-mandelic acid with different enantiomeric ratio were calculated based on integration of proton well-separated splitting signals. Frontiers Media S.A. 2020-05-04 /pmc/articles/PMC7213237/ /pubmed/32432082 http://dx.doi.org/10.3389/fchem.2020.00336 Text en Copyright © 2020 Li, Ma, Wang, Wang and Lei. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Li, Gaowei
Ma, Minshan
Wang, Guifang
Wang, Xiaojuan
Lei, Xinxiang
Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent
title Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent
title_full Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent
title_fullStr Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent
title_full_unstemmed Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent
title_short Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent
title_sort efficient enantiodifferentiation of carboxylic acids using binol-based amino alcohol as a chiral nmr solvating agent
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7213237/
https://www.ncbi.nlm.nih.gov/pubmed/32432082
http://dx.doi.org/10.3389/fchem.2020.00336
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