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Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction
Axially chiral compounds play an important role in areas such as asymmetric catalysis. The tyrosine click-like reaction is an efficient approach for synthesis of urazoles with potential applications in pharmaceutical and asymmetric catalysis. Here we discover a class of urazole with axial chirality...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4753251/ https://www.ncbi.nlm.nih.gov/pubmed/26864510 http://dx.doi.org/10.1038/ncomms10677 |
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author | Zhang, Ji-Wei Xu, Jin-Hui Cheng, Dao-Juan Shi, Chuan Liu, Xin-Yuan Tan, Bin |
author_facet | Zhang, Ji-Wei Xu, Jin-Hui Cheng, Dao-Juan Shi, Chuan Liu, Xin-Yuan Tan, Bin |
author_sort | Zhang, Ji-Wei |
collection | PubMed |
description | Axially chiral compounds play an important role in areas such as asymmetric catalysis. The tyrosine click-like reaction is an efficient approach for synthesis of urazoles with potential applications in pharmaceutical and asymmetric catalysis. Here we discover a class of urazole with axial chirality by restricted rotation around an N–Ar bond. By using bifunctional organocatalyst, we successfully develop an organocatalytic asymmetric tyrosine click-like reaction in high yields with excellent enantioselectivity under mild reaction conditions. The excellent remote enantiocontrol of the strategy originates from the efficient discrimination of the two reactive sites in the triazoledione and transferring the stereochemical information of the catalyst into the axial chirality of urazoles at the remote position far from the reactive site. |
format | Online Article Text |
id | pubmed-4753251 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-47532512016-03-04 Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction Zhang, Ji-Wei Xu, Jin-Hui Cheng, Dao-Juan Shi, Chuan Liu, Xin-Yuan Tan, Bin Nat Commun Article Axially chiral compounds play an important role in areas such as asymmetric catalysis. The tyrosine click-like reaction is an efficient approach for synthesis of urazoles with potential applications in pharmaceutical and asymmetric catalysis. Here we discover a class of urazole with axial chirality by restricted rotation around an N–Ar bond. By using bifunctional organocatalyst, we successfully develop an organocatalytic asymmetric tyrosine click-like reaction in high yields with excellent enantioselectivity under mild reaction conditions. The excellent remote enantiocontrol of the strategy originates from the efficient discrimination of the two reactive sites in the triazoledione and transferring the stereochemical information of the catalyst into the axial chirality of urazoles at the remote position far from the reactive site. Nature Publishing Group 2016-02-11 /pmc/articles/PMC4753251/ /pubmed/26864510 http://dx.doi.org/10.1038/ncomms10677 Text en Copyright © 2016, Nature Publishing Group, a division of Macmillan Publishers Limited. All Rights Reserved. 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 Zhang, Ji-Wei Xu, Jin-Hui Cheng, Dao-Juan Shi, Chuan Liu, Xin-Yuan Tan, Bin Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
title | Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
title_full | Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
title_fullStr | Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
title_full_unstemmed | Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
title_short | Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
title_sort | discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4753251/ https://www.ncbi.nlm.nih.gov/pubmed/26864510 http://dx.doi.org/10.1038/ncomms10677 |
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