A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties

A K(+)-promoted Diels–Alder reaction of 1,4,9,10-anthradiquinone with various dienes is achieved in the presence of a self-assembled macrocyclic boronic ester [2+2](crown) containing two crown ether moieties. The reaction rate is remarkably accelerated (up to 206-fold) compared to that in the absenc...

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Detalles Bibliográficos
Autores principales: Ono, Kosuke, Niibe, Morikazu, Iwasawa, Nobuharu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6761878/
https://www.ncbi.nlm.nih.gov/pubmed/31588314
http://dx.doi.org/10.1039/c9sc01597c
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author Ono, Kosuke
Niibe, Morikazu
Iwasawa, Nobuharu
author_facet Ono, Kosuke
Niibe, Morikazu
Iwasawa, Nobuharu
author_sort Ono, Kosuke
collection PubMed
description A K(+)-promoted Diels–Alder reaction of 1,4,9,10-anthradiquinone with various dienes is achieved in the presence of a self-assembled macrocyclic boronic ester [2+2](crown) containing two crown ether moieties. The reaction rate is remarkably accelerated (up to 206-fold) compared to that in the absence of the promoter. Furthermore, the reaction proceeds regioselectively to yield an internal adduct. The self-assembly protocol was also demonstrated.
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spelling pubmed-67618782019-10-04 A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties Ono, Kosuke Niibe, Morikazu Iwasawa, Nobuharu Chem Sci Chemistry A K(+)-promoted Diels–Alder reaction of 1,4,9,10-anthradiquinone with various dienes is achieved in the presence of a self-assembled macrocyclic boronic ester [2+2](crown) containing two crown ether moieties. The reaction rate is remarkably accelerated (up to 206-fold) compared to that in the absence of the promoter. Furthermore, the reaction proceeds regioselectively to yield an internal adduct. The self-assembly protocol was also demonstrated. Royal Society of Chemistry 2019-07-03 /pmc/articles/PMC6761878/ /pubmed/31588314 http://dx.doi.org/10.1039/c9sc01597c Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ono, Kosuke
Niibe, Morikazu
Iwasawa, Nobuharu
A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
title A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
title_full A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
title_fullStr A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
title_full_unstemmed A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
title_short A K(+)-promoted Diels–Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
title_sort k(+)-promoted diels–alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6761878/
https://www.ncbi.nlm.nih.gov/pubmed/31588314
http://dx.doi.org/10.1039/c9sc01597c
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