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Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction

Compared with the well-developed carbon-stereogenic chemistry, the construction of boron-stereogenic compounds remains undeveloped and challenging. Herein, the previously elusive catalytic enantioselective construction of boron-stereogenic compounds has been achieved through enantioselective desymme...

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Autores principales: Zhang, Guan, Zhang, Zhihan, Hou, Mengyuan, Cai, Xinping, Yang, Kai, Yu, Peiyuan, Song, Qiuling
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9098526/
https://www.ncbi.nlm.nih.gov/pubmed/35552397
http://dx.doi.org/10.1038/s41467-022-30287-7
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author Zhang, Guan
Zhang, Zhihan
Hou, Mengyuan
Cai, Xinping
Yang, Kai
Yu, Peiyuan
Song, Qiuling
author_facet Zhang, Guan
Zhang, Zhihan
Hou, Mengyuan
Cai, Xinping
Yang, Kai
Yu, Peiyuan
Song, Qiuling
author_sort Zhang, Guan
collection PubMed
description Compared with the well-developed carbon-stereogenic chemistry, the construction of boron-stereogenic compounds remains undeveloped and challenging. Herein, the previously elusive catalytic enantioselective construction of boron-stereogenic compounds has been achieved through enantioselective desymmetric B–H bond insertion reaction. The B–H bond insertion reaction of 2-arylpyridine-boranes with versatile diazo compounds under chiral copper catalyst can afford boron-stereogenic compounds with good to excellent enantioselectivity. Moreover, the synthetic utility of this reaction is demonstrated by the scalability and downstream transformations. DFT calculations provide insights into the reaction mechanism and the origin of stereoselectivity.
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spelling pubmed-90985262022-05-14 Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction Zhang, Guan Zhang, Zhihan Hou, Mengyuan Cai, Xinping Yang, Kai Yu, Peiyuan Song, Qiuling Nat Commun Article Compared with the well-developed carbon-stereogenic chemistry, the construction of boron-stereogenic compounds remains undeveloped and challenging. Herein, the previously elusive catalytic enantioselective construction of boron-stereogenic compounds has been achieved through enantioselective desymmetric B–H bond insertion reaction. The B–H bond insertion reaction of 2-arylpyridine-boranes with versatile diazo compounds under chiral copper catalyst can afford boron-stereogenic compounds with good to excellent enantioselectivity. Moreover, the synthetic utility of this reaction is demonstrated by the scalability and downstream transformations. DFT calculations provide insights into the reaction mechanism and the origin of stereoselectivity. Nature Publishing Group UK 2022-05-12 /pmc/articles/PMC9098526/ /pubmed/35552397 http://dx.doi.org/10.1038/s41467-022-30287-7 Text en © The Author(s) 2022 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 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/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Zhang, Guan
Zhang, Zhihan
Hou, Mengyuan
Cai, Xinping
Yang, Kai
Yu, Peiyuan
Song, Qiuling
Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction
title Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction
title_full Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction
title_fullStr Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction
title_full_unstemmed Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction
title_short Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction
title_sort construction of boron-stereogenic compounds via enantioselective cu-catalyzed desymmetric b–h bond insertion reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9098526/
https://www.ncbi.nlm.nih.gov/pubmed/35552397
http://dx.doi.org/10.1038/s41467-022-30287-7
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