Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols

A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal...

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Autores principales: Zhao, Hua, Shen, Peng, Sun, Dongru, Zhai, Hongbin, Zhao, Yufen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8322234/
https://www.ncbi.nlm.nih.gov/pubmed/34336794
http://dx.doi.org/10.3389/fchem.2021.711257
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author Zhao, Hua
Shen, Peng
Sun, Dongru
Zhai, Hongbin
Zhao, Yufen
author_facet Zhao, Hua
Shen, Peng
Sun, Dongru
Zhai, Hongbin
Zhao, Yufen
author_sort Zhao, Hua
collection PubMed
description A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal catalysts or additives. This robust procedure was completed smoothly on a gram-scale to afford the corresponding product with comparable efficiency. Furthermore, the synthetic application of the prepared product has been demonstrated by its transformation into a variety of synthetically useful molecules.
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spelling pubmed-83222342021-07-31 Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols Zhao, Hua Shen, Peng Sun, Dongru Zhai, Hongbin Zhao, Yufen Front Chem Chemistry A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal catalysts or additives. This robust procedure was completed smoothly on a gram-scale to afford the corresponding product with comparable efficiency. Furthermore, the synthetic application of the prepared product has been demonstrated by its transformation into a variety of synthetically useful molecules. Frontiers Media S.A. 2021-07-16 /pmc/articles/PMC8322234/ /pubmed/34336794 http://dx.doi.org/10.3389/fchem.2021.711257 Text en Copyright © 2021 Zhao, Shen, Sun, Zhai and Zhao. https://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
Zhao, Hua
Shen, Peng
Sun, Dongru
Zhai, Hongbin
Zhao, Yufen
Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
title Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
title_full Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
title_fullStr Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
title_full_unstemmed Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
title_short Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
title_sort transition-metal-free [3+2] dehydration cycloaddition of donor-acceptor cyclopropanes with 2-naphthols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8322234/
https://www.ncbi.nlm.nih.gov/pubmed/34336794
http://dx.doi.org/10.3389/fchem.2021.711257
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