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Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis
A strategy for expanding the utility of chiral pyridine‐2,6‐bis(oxazoline) (pybox) ligands for asymmetric transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asymmetric induction. Specifically, a ruthenium(II) pybox fragment is combined wit...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384177/ https://www.ncbi.nlm.nih.gov/pubmed/32394593 http://dx.doi.org/10.1002/anie.202004243 |
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author | Li, Long Han, Feng Nie, Xin Hong, Yubiao Ivlev, Sergei Meggers, Eric |
author_facet | Li, Long Han, Feng Nie, Xin Hong, Yubiao Ivlev, Sergei Meggers, Eric |
author_sort | Li, Long |
collection | PubMed |
description | A strategy for expanding the utility of chiral pyridine‐2,6‐bis(oxazoline) (pybox) ligands for asymmetric transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asymmetric induction. Specifically, a ruthenium(II) pybox fragment is combined with a cyclometalated N‐heterocyclic carbene (NHC) ligand to generate catalysts for enantioselective transition metal nitrenoid chemistry, including ring contraction to chiral 2H‐azirines (up to 97 % ee with 2000 TON) and enantioselective C(sp(3))−H aminations (up to 97 % ee with 50 TON). |
format | Online Article Text |
id | pubmed-7384177 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-73841772020-07-28 Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis Li, Long Han, Feng Nie, Xin Hong, Yubiao Ivlev, Sergei Meggers, Eric Angew Chem Int Ed Engl Communications A strategy for expanding the utility of chiral pyridine‐2,6‐bis(oxazoline) (pybox) ligands for asymmetric transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asymmetric induction. Specifically, a ruthenium(II) pybox fragment is combined with a cyclometalated N‐heterocyclic carbene (NHC) ligand to generate catalysts for enantioselective transition metal nitrenoid chemistry, including ring contraction to chiral 2H‐azirines (up to 97 % ee with 2000 TON) and enantioselective C(sp(3))−H aminations (up to 97 % ee with 50 TON). John Wiley and Sons Inc. 2020-06-05 2020-07-20 /pmc/articles/PMC7384177/ /pubmed/32394593 http://dx.doi.org/10.1002/anie.202004243 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Li, Long Han, Feng Nie, Xin Hong, Yubiao Ivlev, Sergei Meggers, Eric Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis |
title | Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis |
title_full | Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis |
title_fullStr | Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis |
title_full_unstemmed | Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis |
title_short | Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis |
title_sort | complementing pyridine‐2,6‐bis(oxazoline) with cyclometalated n‐heterocyclic carbene for asymmetric ruthenium catalysis |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384177/ https://www.ncbi.nlm.nih.gov/pubmed/32394593 http://dx.doi.org/10.1002/anie.202004243 |
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