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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...

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Autores principales: Li, Zhiyang, Li, Yichen, Li, Xingguang, Wu, Mandi, He, Ming-Liang, Sun, Jianwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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.
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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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