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Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three‐dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)‐NHC‐catalyzed asymmetric hydrogenation of 2‐quinolones under mild reaction conditions....

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Detalles Bibliográficos
Autores principales: Hu, Tianjiao, Lückemeier, Lukas, Daniliuc, Constantin, Glorius, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8596914/
https://www.ncbi.nlm.nih.gov/pubmed/34460127
http://dx.doi.org/10.1002/anie.202108503
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author Hu, Tianjiao
Lückemeier, Lukas
Daniliuc, Constantin
Glorius, Frank
author_facet Hu, Tianjiao
Lückemeier, Lukas
Daniliuc, Constantin
Glorius, Frank
author_sort Hu, Tianjiao
collection PubMed
description Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three‐dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)‐NHC‐catalyzed asymmetric hydrogenation of 2‐quinolones under mild reaction conditions. Alkyl‐, aryl‐ and halogen‐substituted optically active dihydro‐2‐quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom‐economic pathway to construct simple chiral 3,4‐dihydro‐2‐quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
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spelling pubmed-85969142021-11-22 Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones Hu, Tianjiao Lückemeier, Lukas Daniliuc, Constantin Glorius, Frank Angew Chem Int Ed Engl Communications Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three‐dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)‐NHC‐catalyzed asymmetric hydrogenation of 2‐quinolones under mild reaction conditions. Alkyl‐, aryl‐ and halogen‐substituted optically active dihydro‐2‐quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom‐economic pathway to construct simple chiral 3,4‐dihydro‐2‐quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones. John Wiley and Sons Inc. 2021-09-22 2021-10-18 /pmc/articles/PMC8596914/ /pubmed/34460127 http://dx.doi.org/10.1002/anie.202108503 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Hu, Tianjiao
Lückemeier, Lukas
Daniliuc, Constantin
Glorius, Frank
Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
title Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
title_full Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
title_fullStr Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
title_full_unstemmed Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
title_short Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
title_sort ru‐nhc‐catalyzed asymmetric hydrogenation of 2‐quinolones to chiral 3,4‐dihydro‐2‐quinolones
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8596914/
https://www.ncbi.nlm.nih.gov/pubmed/34460127
http://dx.doi.org/10.1002/anie.202108503
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