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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...

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Autores principales: Jin, Shengzhou, Wang, Jia-Ying, Tang, Yao, Rouh, Hossein, Zhang, Sai, Xu, Ting, Wang, Yu, Yuan, Qingkai, Chen, Daixiang, Unruh, Daniel, Li, Guigen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
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.
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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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