Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivit...

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Autores principales: Fujita, Rie, Hanaya, Kengo, Sugai, Takeshi, Higashibayashi, Shuhei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8674349/
https://www.ncbi.nlm.nih.gov/pubmed/34911981
http://dx.doi.org/10.1038/s41598-021-03448-9
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author Fujita, Rie
Hanaya, Kengo
Sugai, Takeshi
Higashibayashi, Shuhei
author_facet Fujita, Rie
Hanaya, Kengo
Sugai, Takeshi
Higashibayashi, Shuhei
author_sort Fujita, Rie
collection PubMed
description Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine.
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spelling pubmed-86743492021-12-20 Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine Fujita, Rie Hanaya, Kengo Sugai, Takeshi Higashibayashi, Shuhei Sci Rep Article Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine. Nature Publishing Group UK 2021-12-15 /pmc/articles/PMC8674349/ /pubmed/34911981 http://dx.doi.org/10.1038/s41598-021-03448-9 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Fujita, Rie
Hanaya, Kengo
Sugai, Takeshi
Higashibayashi, Shuhei
Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
title Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
title_full Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
title_fullStr Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
title_full_unstemmed Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
title_short Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
title_sort chemoselectivity-independent cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8674349/
https://www.ncbi.nlm.nih.gov/pubmed/34911981
http://dx.doi.org/10.1038/s41598-021-03448-9
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