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Chiral proline-substituted porous organic cages in asymmetric organocatalysis
The efficient preparation of chiral porous organic cages (POCs) with specific functions is challenging, and their application in asymmetric catalysis has not previously been explored. In this work, we have achieved the construction of chiral POCs based on a supramolecular tetraformyl-resorcin[4]aren...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8943855/ https://www.ncbi.nlm.nih.gov/pubmed/35432868 http://dx.doi.org/10.1039/d2sc00395c |
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author | Xu, Ning Su, Kongzhao El-Sayed, El-Sayed M. Ju, Zhanfeng Yuan, Daqiang |
author_facet | Xu, Ning Su, Kongzhao El-Sayed, El-Sayed M. Ju, Zhanfeng Yuan, Daqiang |
author_sort | Xu, Ning |
collection | PubMed |
description | The efficient preparation of chiral porous organic cages (POCs) with specific functions is challenging, and their application in asymmetric catalysis has not previously been explored. In this work, we have achieved the construction of chiral POCs based on a supramolecular tetraformyl-resorcin[4]arene scaffold with different chiral proline-modified diamine ligands and utilizing dynamic imine chemistry. The incorporation of V-shaped or linear chiral diamines affords the [4 + 8] square prism and [6 + 12] octahedral POCs respectively. The appended chiral proline moieties in such POCs make them highly active supramolecular nanoreactors for asymmetric aldol reactions, delivering up to 92% ee. The spatial distribution of chiral catalytic sites in these two types of POCs greatly affects their catalytic activities and enantioselectivities. This work not only lays a foundation for the asymmetric catalytic application of chiral POCs, but also contributes to our understanding of the catalytic function of biomimetic supramolecular systems. |
format | Online Article Text |
id | pubmed-8943855 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-89438552022-04-14 Chiral proline-substituted porous organic cages in asymmetric organocatalysis Xu, Ning Su, Kongzhao El-Sayed, El-Sayed M. Ju, Zhanfeng Yuan, Daqiang Chem Sci Chemistry The efficient preparation of chiral porous organic cages (POCs) with specific functions is challenging, and their application in asymmetric catalysis has not previously been explored. In this work, we have achieved the construction of chiral POCs based on a supramolecular tetraformyl-resorcin[4]arene scaffold with different chiral proline-modified diamine ligands and utilizing dynamic imine chemistry. The incorporation of V-shaped or linear chiral diamines affords the [4 + 8] square prism and [6 + 12] octahedral POCs respectively. The appended chiral proline moieties in such POCs make them highly active supramolecular nanoreactors for asymmetric aldol reactions, delivering up to 92% ee. The spatial distribution of chiral catalytic sites in these two types of POCs greatly affects their catalytic activities and enantioselectivities. This work not only lays a foundation for the asymmetric catalytic application of chiral POCs, but also contributes to our understanding of the catalytic function of biomimetic supramolecular systems. The Royal Society of Chemistry 2022-03-03 /pmc/articles/PMC8943855/ /pubmed/35432868 http://dx.doi.org/10.1039/d2sc00395c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Xu, Ning Su, Kongzhao El-Sayed, El-Sayed M. Ju, Zhanfeng Yuan, Daqiang Chiral proline-substituted porous organic cages in asymmetric organocatalysis |
title | Chiral proline-substituted porous organic cages in asymmetric organocatalysis |
title_full | Chiral proline-substituted porous organic cages in asymmetric organocatalysis |
title_fullStr | Chiral proline-substituted porous organic cages in asymmetric organocatalysis |
title_full_unstemmed | Chiral proline-substituted porous organic cages in asymmetric organocatalysis |
title_short | Chiral proline-substituted porous organic cages in asymmetric organocatalysis |
title_sort | chiral proline-substituted porous organic cages in asymmetric organocatalysis |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8943855/ https://www.ncbi.nlm.nih.gov/pubmed/35432868 http://dx.doi.org/10.1039/d2sc00395c |
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