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Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones

The axially chiral arylquinazolinone acts as a privileged structural scaffold, which is present in a large number of natural products and biologically active compounds as well as in chiral ligands. However, a direct catalytic enantioselective approach to access optically pure arylquinazolinones has...

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Autores principales: Wang, Yong-Bin, Zheng, Sheng-Cai, Hu, Yu-Mei, Tan, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5454535/
https://www.ncbi.nlm.nih.gov/pubmed/28524863
http://dx.doi.org/10.1038/ncomms15489
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author Wang, Yong-Bin
Zheng, Sheng-Cai
Hu, Yu-Mei
Tan, Bin
author_facet Wang, Yong-Bin
Zheng, Sheng-Cai
Hu, Yu-Mei
Tan, Bin
author_sort Wang, Yong-Bin
collection PubMed
description The axially chiral arylquinazolinone acts as a privileged structural scaffold, which is present in a large number of natural products and biologically active compounds as well as in chiral ligands. However, a direct catalytic enantioselective approach to access optically pure arylquinazolinones has been underexplored. Here we show a general and efficient approach to access enantiomerically pure arylquinazolinones in one-pot fashion catalysed by chiral phosphoric acids. A variety of axially chiral arylquinazolinones were obtained in high yields with good to excellent enantioselectivities under mild condition. Furthermore, we disclosed a method for atroposelective synthesis of alkyl-substituted arylquinazolinones involving Brønsted acid-catalysed carbon–carbon bond cleavage strategy. Finally, the asymmetric total synthesis of eupolyphagin bearing a cyclic arylquinazolinone skeleton was accomplished with an overall yield of 32% in six steps by utilizing the aforementioned methodology.
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spelling pubmed-54545352017-06-07 Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones Wang, Yong-Bin Zheng, Sheng-Cai Hu, Yu-Mei Tan, Bin Nat Commun Article The axially chiral arylquinazolinone acts as a privileged structural scaffold, which is present in a large number of natural products and biologically active compounds as well as in chiral ligands. However, a direct catalytic enantioselective approach to access optically pure arylquinazolinones has been underexplored. Here we show a general and efficient approach to access enantiomerically pure arylquinazolinones in one-pot fashion catalysed by chiral phosphoric acids. A variety of axially chiral arylquinazolinones were obtained in high yields with good to excellent enantioselectivities under mild condition. Furthermore, we disclosed a method for atroposelective synthesis of alkyl-substituted arylquinazolinones involving Brønsted acid-catalysed carbon–carbon bond cleavage strategy. Finally, the asymmetric total synthesis of eupolyphagin bearing a cyclic arylquinazolinone skeleton was accomplished with an overall yield of 32% in six steps by utilizing the aforementioned methodology. Nature Publishing Group 2017-05-19 /pmc/articles/PMC5454535/ /pubmed/28524863 http://dx.doi.org/10.1038/ncomms15489 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Wang, Yong-Bin
Zheng, Sheng-Cai
Hu, Yu-Mei
Tan, Bin
Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
title Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
title_full Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
title_fullStr Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
title_full_unstemmed Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
title_short Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
title_sort brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5454535/
https://www.ncbi.nlm.nih.gov/pubmed/28524863
http://dx.doi.org/10.1038/ncomms15489
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