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Chirality Sensing of N-Heterocycles via (19)F NMR

[Image: see text] Methods to rapidly detect and differentiate chiral N-heterocyclic compounds become increasingly important owing to the widespread application of N-heterocycles in drug discovery and materials science. We herein report a (19)F NMR-based chemosensing approach for the prompt enantioan...

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Autores principales: Gu, Guangxing, Xu, Zhenchuang, Wen, Lixian, Liang, Jinhua, Wang, Chenyang, Wan, Xiaolong, Zhao, Yanchuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10206601/
https://www.ncbi.nlm.nih.gov/pubmed/37234104
http://dx.doi.org/10.1021/jacsau.2c00661
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author Gu, Guangxing
Xu, Zhenchuang
Wen, Lixian
Liang, Jinhua
Wang, Chenyang
Wan, Xiaolong
Zhao, Yanchuan
author_facet Gu, Guangxing
Xu, Zhenchuang
Wen, Lixian
Liang, Jinhua
Wang, Chenyang
Wan, Xiaolong
Zhao, Yanchuan
author_sort Gu, Guangxing
collection PubMed
description [Image: see text] Methods to rapidly detect and differentiate chiral N-heterocyclic compounds become increasingly important owing to the widespread application of N-heterocycles in drug discovery and materials science. We herein report a (19)F NMR-based chemosensing approach for the prompt enantioanalysis of various N-heterocycles, where the dynamic binding between the analytes and a chiral (19)F-labeled palladium probe create characteristic (19)F NMR signals assignable to each enantiomer. The open binding site of the probe allows the effective recognition of bulky analytes that are otherwise difficult to detect. The chirality center distal to the binding site is found sufficient for the probe to discriminate the stereoconfiguration of the analyte. The utility of the method in the screening of reaction conditions for the asymmetric synthesis of lansoprazole is demonstrated.
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spelling pubmed-102066012023-05-25 Chirality Sensing of N-Heterocycles via (19)F NMR Gu, Guangxing Xu, Zhenchuang Wen, Lixian Liang, Jinhua Wang, Chenyang Wan, Xiaolong Zhao, Yanchuan JACS Au [Image: see text] Methods to rapidly detect and differentiate chiral N-heterocyclic compounds become increasingly important owing to the widespread application of N-heterocycles in drug discovery and materials science. We herein report a (19)F NMR-based chemosensing approach for the prompt enantioanalysis of various N-heterocycles, where the dynamic binding between the analytes and a chiral (19)F-labeled palladium probe create characteristic (19)F NMR signals assignable to each enantiomer. The open binding site of the probe allows the effective recognition of bulky analytes that are otherwise difficult to detect. The chirality center distal to the binding site is found sufficient for the probe to discriminate the stereoconfiguration of the analyte. The utility of the method in the screening of reaction conditions for the asymmetric synthesis of lansoprazole is demonstrated. American Chemical Society 2023-05-02 /pmc/articles/PMC10206601/ /pubmed/37234104 http://dx.doi.org/10.1021/jacsau.2c00661 Text en © 2023 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 Gu, Guangxing
Xu, Zhenchuang
Wen, Lixian
Liang, Jinhua
Wang, Chenyang
Wan, Xiaolong
Zhao, Yanchuan
Chirality Sensing of N-Heterocycles via (19)F NMR
title Chirality Sensing of N-Heterocycles via (19)F NMR
title_full Chirality Sensing of N-Heterocycles via (19)F NMR
title_fullStr Chirality Sensing of N-Heterocycles via (19)F NMR
title_full_unstemmed Chirality Sensing of N-Heterocycles via (19)F NMR
title_short Chirality Sensing of N-Heterocycles via (19)F NMR
title_sort chirality sensing of n-heterocycles via (19)f nmr
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10206601/
https://www.ncbi.nlm.nih.gov/pubmed/37234104
http://dx.doi.org/10.1021/jacsau.2c00661
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