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Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts

[Image: see text] A new class of recyclable supported chiral heterogeneous ligands has been synthesized by the reaction of functionalized mesoporous SBA-15 with aliphatic- and aromatic-substituted chiral amino oxazoline ligands. The obtained chiral heterogeneous ligands were characterized by several...

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Autores principales: Samadi, Saadi, Ashouri, Akram, Samadi, Mojgan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7482298/
https://www.ncbi.nlm.nih.gov/pubmed/32923794
http://dx.doi.org/10.1021/acsomega.0c02764
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author Samadi, Saadi
Ashouri, Akram
Samadi, Mojgan
author_facet Samadi, Saadi
Ashouri, Akram
Samadi, Mojgan
author_sort Samadi, Saadi
collection PubMed
description [Image: see text] A new class of recyclable supported chiral heterogeneous ligands has been synthesized by the reaction of functionalized mesoporous SBA-15 with aliphatic- and aromatic-substituted chiral amino oxazoline ligands. The obtained chiral heterogeneous ligands were characterized by several techniques such as Fourier transform infrared, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and BET–BJH. The application of these new heterogeneous ligands in copper-catalyzed asymmetric allylic oxidation of olefins by using perester showed better yields up to 95% and better enantioselectivities up to 96% compared to the corresponding homogeneous catalysts. These findings can be considered as an important step in the advancement of green chemistry. Investigation of the recyclability of the catalysts confirmed that they were easily recovered and reused eight times without significant losses in reactivity, yield, and enantioselectivity.
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spelling pubmed-74822982020-09-11 Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts Samadi, Saadi Ashouri, Akram Samadi, Mojgan ACS Omega [Image: see text] A new class of recyclable supported chiral heterogeneous ligands has been synthesized by the reaction of functionalized mesoporous SBA-15 with aliphatic- and aromatic-substituted chiral amino oxazoline ligands. The obtained chiral heterogeneous ligands were characterized by several techniques such as Fourier transform infrared, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and BET–BJH. The application of these new heterogeneous ligands in copper-catalyzed asymmetric allylic oxidation of olefins by using perester showed better yields up to 95% and better enantioselectivities up to 96% compared to the corresponding homogeneous catalysts. These findings can be considered as an important step in the advancement of green chemistry. Investigation of the recyclability of the catalysts confirmed that they were easily recovered and reused eight times without significant losses in reactivity, yield, and enantioselectivity. American Chemical Society 2020-08-24 /pmc/articles/PMC7482298/ /pubmed/32923794 http://dx.doi.org/10.1021/acsomega.0c02764 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Samadi, Saadi
Ashouri, Akram
Samadi, Mojgan
Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts
title Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts
title_full Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts
title_fullStr Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts
title_full_unstemmed Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts
title_short Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts
title_sort synthesis of chiral allylic esters by using the new recyclable chiral heterogeneous oxazoline-based catalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7482298/
https://www.ncbi.nlm.nih.gov/pubmed/32923794
http://dx.doi.org/10.1021/acsomega.0c02764
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