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Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with N-Aryl Imines: Synthesis of Tetrahydroquinolines
[Image: see text] A one-pot gold-catalyzed hydroalkoxylation/Povarov reaction cascade of alkynols with N-aryl imines or in situ generated iminium has been developed. The protocol provides a facile access to a series of fused tricyclic tetrahydroquinolines with a broad substrate scope using readily a...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6761745/ https://www.ncbi.nlm.nih.gov/pubmed/31572879 http://dx.doi.org/10.1021/acsomega.9b02693 |
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author | He, Ciwang Cai, Ju Zheng, Yang Pei, Chao Qiu, Lihua Xu, Xinfang |
author_facet | He, Ciwang Cai, Ju Zheng, Yang Pei, Chao Qiu, Lihua Xu, Xinfang |
author_sort | He, Ciwang |
collection | PubMed |
description | [Image: see text] A one-pot gold-catalyzed hydroalkoxylation/Povarov reaction cascade of alkynols with N-aryl imines or in situ generated iminium has been developed. The protocol provides a facile access to a series of fused tricyclic tetrahydroquinolines with a broad substrate scope using readily available materials under mild conditions. The unique mechanistic feature is the dual function of the gold catalyst, which first catalyzed the intramolecular hydroalkoxylation of alkynols, and upon the formation of dihydrofuran species, promoted the following Povarov reaction with high stereoselectivity. |
format | Online Article Text |
id | pubmed-6761745 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-67617452019-09-30 Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with N-Aryl Imines: Synthesis of Tetrahydroquinolines He, Ciwang Cai, Ju Zheng, Yang Pei, Chao Qiu, Lihua Xu, Xinfang ACS Omega [Image: see text] A one-pot gold-catalyzed hydroalkoxylation/Povarov reaction cascade of alkynols with N-aryl imines or in situ generated iminium has been developed. The protocol provides a facile access to a series of fused tricyclic tetrahydroquinolines with a broad substrate scope using readily available materials under mild conditions. The unique mechanistic feature is the dual function of the gold catalyst, which first catalyzed the intramolecular hydroalkoxylation of alkynols, and upon the formation of dihydrofuran species, promoted the following Povarov reaction with high stereoselectivity. American Chemical Society 2019-09-09 /pmc/articles/PMC6761745/ /pubmed/31572879 http://dx.doi.org/10.1021/acsomega.9b02693 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | He, Ciwang Cai, Ju Zheng, Yang Pei, Chao Qiu, Lihua Xu, Xinfang Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with N-Aryl Imines: Synthesis of Tetrahydroquinolines |
title | Gold-Catalyzed Hydroalkoxylation/Povarov Reaction
Cascade of Alkynols with N-Aryl Imines: Synthesis
of Tetrahydroquinolines |
title_full | Gold-Catalyzed Hydroalkoxylation/Povarov Reaction
Cascade of Alkynols with N-Aryl Imines: Synthesis
of Tetrahydroquinolines |
title_fullStr | Gold-Catalyzed Hydroalkoxylation/Povarov Reaction
Cascade of Alkynols with N-Aryl Imines: Synthesis
of Tetrahydroquinolines |
title_full_unstemmed | Gold-Catalyzed Hydroalkoxylation/Povarov Reaction
Cascade of Alkynols with N-Aryl Imines: Synthesis
of Tetrahydroquinolines |
title_short | Gold-Catalyzed Hydroalkoxylation/Povarov Reaction
Cascade of Alkynols with N-Aryl Imines: Synthesis
of Tetrahydroquinolines |
title_sort | gold-catalyzed hydroalkoxylation/povarov reaction
cascade of alkynols with n-aryl imines: synthesis
of tetrahydroquinolines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6761745/ https://www.ncbi.nlm.nih.gov/pubmed/31572879 http://dx.doi.org/10.1021/acsomega.9b02693 |
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