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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2017
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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. |
format | Online Article Text |
id | pubmed-5454535 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
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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