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Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
[Image: see text] Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir–N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both th...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884017/ https://www.ncbi.nlm.nih.gov/pubmed/33351634 http://dx.doi.org/10.1021/acs.orglett.0c04012 |
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author | Peters, Bram B. C. Jongcharoenkamol, Jira Krajangsri, Suppachai Andersson, Pher G. |
author_facet | Peters, Bram B. C. Jongcharoenkamol, Jira Krajangsri, Suppachai Andersson, Pher G. |
author_sort | Peters, Bram B. C. |
collection | PubMed |
description | [Image: see text] Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir–N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion. |
format | Online Article Text |
id | pubmed-7884017 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-78840172021-02-16 Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones Peters, Bram B. C. Jongcharoenkamol, Jira Krajangsri, Suppachai Andersson, Pher G. Org Lett [Image: see text] Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir–N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion. American Chemical Society 2020-12-22 2021-01-01 /pmc/articles/PMC7884017/ /pubmed/33351634 http://dx.doi.org/10.1021/acs.orglett.0c04012 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Peters, Bram B. C. Jongcharoenkamol, Jira Krajangsri, Suppachai Andersson, Pher G. Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones |
title | Highly Enantioselective Iridium-Catalyzed Hydrogenation
of Conjugated Trisubstituted Enones |
title_full | Highly Enantioselective Iridium-Catalyzed Hydrogenation
of Conjugated Trisubstituted Enones |
title_fullStr | Highly Enantioselective Iridium-Catalyzed Hydrogenation
of Conjugated Trisubstituted Enones |
title_full_unstemmed | Highly Enantioselective Iridium-Catalyzed Hydrogenation
of Conjugated Trisubstituted Enones |
title_short | Highly Enantioselective Iridium-Catalyzed Hydrogenation
of Conjugated Trisubstituted Enones |
title_sort | highly enantioselective iridium-catalyzed hydrogenation
of conjugated trisubstituted enones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884017/ https://www.ncbi.nlm.nih.gov/pubmed/33351634 http://dx.doi.org/10.1021/acs.orglett.0c04012 |
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