Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis

Multicomponent reactions (MCRs) facilitate the rapid and diverse construction of molecular scaffolds with modularity and step economy. In this work, engagement of boronic acids as carbon nucleophiles culminates in a Passerini-type three-component coupling reaction towards the synthesis of an expande...

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Autores principales: Yang, Kai, Zhang, Feng, Fang, Tongchang, Li, Chaokun, Li, Wangyang, Song, Qiuling
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/PMC7815879/
https://www.ncbi.nlm.nih.gov/pubmed/33469014
http://dx.doi.org/10.1038/s41467-020-20727-7
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author Yang, Kai
Zhang, Feng
Fang, Tongchang
Li, Chaokun
Li, Wangyang
Song, Qiuling
author_facet Yang, Kai
Zhang, Feng
Fang, Tongchang
Li, Chaokun
Li, Wangyang
Song, Qiuling
author_sort Yang, Kai
collection PubMed
description Multicomponent reactions (MCRs) facilitate the rapid and diverse construction of molecular scaffolds with modularity and step economy. In this work, engagement of boronic acids as carbon nucleophiles culminates in a Passerini-type three-component coupling reaction towards the synthesis of an expanded inventory of α-hydroxyketones with skeletal diversity. In addition to the appealing features of MCRs, this protocol portrays good functional group tolerance, broad substrate scope under mild conditions and operational simplicity. The utility of this chemistry is further demonstrated by amenable modifications of bioactive products and pharmaceuticals as well as in the functionalization of products to useful compounds.
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spelling pubmed-78158792021-01-28 Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis Yang, Kai Zhang, Feng Fang, Tongchang Li, Chaokun Li, Wangyang Song, Qiuling Nat Commun Article Multicomponent reactions (MCRs) facilitate the rapid and diverse construction of molecular scaffolds with modularity and step economy. In this work, engagement of boronic acids as carbon nucleophiles culminates in a Passerini-type three-component coupling reaction towards the synthesis of an expanded inventory of α-hydroxyketones with skeletal diversity. In addition to the appealing features of MCRs, this protocol portrays good functional group tolerance, broad substrate scope under mild conditions and operational simplicity. The utility of this chemistry is further demonstrated by amenable modifications of bioactive products and pharmaceuticals as well as in the functionalization of products to useful compounds. Nature Publishing Group UK 2021-01-19 /pmc/articles/PMC7815879/ /pubmed/33469014 http://dx.doi.org/10.1038/s41467-020-20727-7 Text en © The Author(s) 2021 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 license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license 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 license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Yang, Kai
Zhang, Feng
Fang, Tongchang
Li, Chaokun
Li, Wangyang
Song, Qiuling
Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
title Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
title_full Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
title_fullStr Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
title_full_unstemmed Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
title_short Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
title_sort passerini-type reaction of boronic acids enables α-hydroxyketones synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7815879/
https://www.ncbi.nlm.nih.gov/pubmed/33469014
http://dx.doi.org/10.1038/s41467-020-20727-7
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