Cargando…
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....
Autores principales: | , , , |
---|---|
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 |
_version_ | 1784600496203366400 |
---|---|
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. |
format | Online Article Text |
id | pubmed-8596914 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT hutianjiao runhccatalyzedasymmetrichydrogenationof2quinolonestochiral34dihydro2quinolones AT luckemeierlukas runhccatalyzedasymmetrichydrogenationof2quinolonestochiral34dihydro2quinolones AT daniliucconstantin runhccatalyzedasymmetrichydrogenationof2quinolonestochiral34dihydro2quinolones AT gloriusfrank runhccatalyzedasymmetrichydrogenationof2quinolonestochiral34dihydro2quinolones |