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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...

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Autores principales: Peters, Bram B. C., Jongcharoenkamol, Jira, Krajangsri, Suppachai, Andersson, Pher G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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.
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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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