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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...

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Autores principales: He, Ciwang, Cai, Ju, Zheng, Yang, Pei, Chao, Qiu, Lihua, Xu, Xinfang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
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.
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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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