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Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

[Image: see text] The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands re...

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Autores principales: Connon, Robert, Roche, Brendan, Rokade, Balaji V., Guiry, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8277118/
https://www.ncbi.nlm.nih.gov/pubmed/34019404
http://dx.doi.org/10.1021/acs.chemrev.0c00844
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author Connon, Robert
Roche, Brendan
Rokade, Balaji V.
Guiry, Patrick J.
author_facet Connon, Robert
Roche, Brendan
Rokade, Balaji V.
Guiry, Patrick J.
author_sort Connon, Robert
collection PubMed
description [Image: see text] The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ees for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.
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spelling pubmed-82771182021-07-14 Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis Connon, Robert Roche, Brendan Rokade, Balaji V. Guiry, Patrick J. Chem Rev [Image: see text] The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ees for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations. American Chemical Society 2021-05-21 2021-06-09 /pmc/articles/PMC8277118/ /pubmed/34019404 http://dx.doi.org/10.1021/acs.chemrev.0c00844 Text en © 2021 American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Connon, Robert
Roche, Brendan
Rokade, Balaji V.
Guiry, Patrick J.
Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis
title Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis
title_full Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis
title_fullStr Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis
title_full_unstemmed Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis
title_short Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis
title_sort further developments and applications of oxazoline-containing ligands in asymmetric catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8277118/
https://www.ncbi.nlm.nih.gov/pubmed/34019404
http://dx.doi.org/10.1021/acs.chemrev.0c00844
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