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Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters
A new catalytic asymmetric formal cross dehydrogenative coupling process for the construction of all-aryl quaternary stereocenters is disclosed, which provides access to rarely explored chiral tetraarylmethanes with excellent enantioselectivity. The suitable oxidation conditions and the hydrogen-bon...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8442720/ https://www.ncbi.nlm.nih.gov/pubmed/34659717 http://dx.doi.org/10.1039/d1sc03324g |
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author | Li, Zhiyang Li, Yichen Li, Xingguang Wu, Mandi He, Ming-Liang Sun, Jianwei |
author_facet | Li, Zhiyang Li, Yichen Li, Xingguang Wu, Mandi He, Ming-Liang Sun, Jianwei |
author_sort | Li, Zhiyang |
collection | PubMed |
description | A new catalytic asymmetric formal cross dehydrogenative coupling process for the construction of all-aryl quaternary stereocenters is disclosed, which provides access to rarely explored chiral tetraarylmethanes with excellent enantioselectivity. The suitable oxidation conditions and the hydrogen-bond-based organocatalysis have enabled efficient intermolecular C–C bond formation in an overwhelmingly crowded environment under mild conditions. para-Quinone methides bearing an ortho-directing group serve as the key intermediate. The precise loading of DDQ is critical to the high enantioselectivity. The chiral products have also been demonstrated as promising antiviral agents. |
format | Online Article Text |
id | pubmed-8442720 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-84427202021-10-14 Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters Li, Zhiyang Li, Yichen Li, Xingguang Wu, Mandi He, Ming-Liang Sun, Jianwei Chem Sci Chemistry A new catalytic asymmetric formal cross dehydrogenative coupling process for the construction of all-aryl quaternary stereocenters is disclosed, which provides access to rarely explored chiral tetraarylmethanes with excellent enantioselectivity. The suitable oxidation conditions and the hydrogen-bond-based organocatalysis have enabled efficient intermolecular C–C bond formation in an overwhelmingly crowded environment under mild conditions. para-Quinone methides bearing an ortho-directing group serve as the key intermediate. The precise loading of DDQ is critical to the high enantioselectivity. The chiral products have also been demonstrated as promising antiviral agents. The Royal Society of Chemistry 2021-07-29 /pmc/articles/PMC8442720/ /pubmed/34659717 http://dx.doi.org/10.1039/d1sc03324g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Li, Zhiyang Li, Yichen Li, Xingguang Wu, Mandi He, Ming-Liang Sun, Jianwei Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
title | Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
title_full | Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
title_fullStr | Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
title_full_unstemmed | Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
title_short | Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
title_sort | organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8442720/ https://www.ncbi.nlm.nih.gov/pubmed/34659717 http://dx.doi.org/10.1039/d1sc03324g |
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