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Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges
New multilayer 3D chiral molecules have been designed and synthesized asymmetrically through the strategy of center-to-multilayer folding chirality control and double Suzuki couplings. Individual diastereoisomers were readily obtained and separated via flash column chromatography. The key diastereoi...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9010227/ https://www.ncbi.nlm.nih.gov/pubmed/35433628 http://dx.doi.org/10.3389/fchem.2022.860398 |
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author | Jin, Shengzhou Wang, Jia-Ying Tang, Yao Rouh, Hossein Zhang, Sai Xu, Ting Wang, Yu Yuan, Qingkai Chen, Daixiang Unruh, Daniel Li, Guigen |
author_facet | Jin, Shengzhou Wang, Jia-Ying Tang, Yao Rouh, Hossein Zhang, Sai Xu, Ting Wang, Yu Yuan, Qingkai Chen, Daixiang Unruh, Daniel Li, Guigen |
author_sort | Jin, Shengzhou |
collection | PubMed |
description | New multilayer 3D chiral molecules have been designed and synthesized asymmetrically through the strategy of center-to-multilayer folding chirality control and double Suzuki couplings. Individual diastereoisomers were readily obtained and separated via flash column chromatography. The key diastereoisomer was further converted into corresponding enantiomers. These enantiomers possess electron-deficient aromatic bridges layered with top and bottom aromatic scaffolds. X-ray structural analysis has unambiguously confirmed the configuration, and intermolecular packing results in regular planar patterns in solid crystals. The synthesis was achieved in a total of ten steps starting from commercially available starting materials. |
format | Online Article Text |
id | pubmed-9010227 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-90102272022-04-16 Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges Jin, Shengzhou Wang, Jia-Ying Tang, Yao Rouh, Hossein Zhang, Sai Xu, Ting Wang, Yu Yuan, Qingkai Chen, Daixiang Unruh, Daniel Li, Guigen Front Chem Chemistry New multilayer 3D chiral molecules have been designed and synthesized asymmetrically through the strategy of center-to-multilayer folding chirality control and double Suzuki couplings. Individual diastereoisomers were readily obtained and separated via flash column chromatography. The key diastereoisomer was further converted into corresponding enantiomers. These enantiomers possess electron-deficient aromatic bridges layered with top and bottom aromatic scaffolds. X-ray structural analysis has unambiguously confirmed the configuration, and intermolecular packing results in regular planar patterns in solid crystals. The synthesis was achieved in a total of ten steps starting from commercially available starting materials. Frontiers Media S.A. 2022-03-31 /pmc/articles/PMC9010227/ /pubmed/35433628 http://dx.doi.org/10.3389/fchem.2022.860398 Text en Copyright © 2022 Jin, Wang, Tang, Rouh, Zhang, Xu, Wang, Yuan, Chen, Unruh and Li. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Jin, Shengzhou Wang, Jia-Ying Tang, Yao Rouh, Hossein Zhang, Sai Xu, Ting Wang, Yu Yuan, Qingkai Chen, Daixiang Unruh, Daniel Li, Guigen Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges |
title | Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges |
title_full | Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges |
title_fullStr | Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges |
title_full_unstemmed | Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges |
title_short | Central-to-Folding Chirality Control: Asymmetric Synthesis of Multilayer 3D Targets With Electron-Deficient Bridges |
title_sort | central-to-folding chirality control: asymmetric synthesis of multilayer 3d targets with electron-deficient bridges |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9010227/ https://www.ncbi.nlm.nih.gov/pubmed/35433628 http://dx.doi.org/10.3389/fchem.2022.860398 |
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