Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides

[Image: see text] Under Rh(I) catalysis, α-ketoamides undergo intermolecular hydroacylation with aliphatic aldehydes. A newly designed Josiphos ligand enables access to α-acyloxyamides with high atom-economy and enantioselectivity. On the basis of mechanistic and kinetic studies, we propose a pathwa...

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Autores principales: Kou, Kevin G. M., Le, Diane N., Dong, Vy M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4091274/
https://www.ncbi.nlm.nih.gov/pubmed/24937681
http://dx.doi.org/10.1021/ja504296x
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author Kou, Kevin G. M.
Le, Diane N.
Dong, Vy M.
author_facet Kou, Kevin G. M.
Le, Diane N.
Dong, Vy M.
author_sort Kou, Kevin G. M.
collection PubMed
description [Image: see text] Under Rh(I) catalysis, α-ketoamides undergo intermolecular hydroacylation with aliphatic aldehydes. A newly designed Josiphos ligand enables access to α-acyloxyamides with high atom-economy and enantioselectivity. On the basis of mechanistic and kinetic studies, we propose a pathway in which rhodium plays a dual role in activating the aldehyde for cross-coupling. A stereochemical model is provided to rationalize the sense of enantioinduction observed.
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spelling pubmed-40912742015-06-17 Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides Kou, Kevin G. M. Le, Diane N. Dong, Vy M. J Am Chem Soc [Image: see text] Under Rh(I) catalysis, α-ketoamides undergo intermolecular hydroacylation with aliphatic aldehydes. A newly designed Josiphos ligand enables access to α-acyloxyamides with high atom-economy and enantioselectivity. On the basis of mechanistic and kinetic studies, we propose a pathway in which rhodium plays a dual role in activating the aldehyde for cross-coupling. A stereochemical model is provided to rationalize the sense of enantioinduction observed. American Chemical Society 2014-06-17 2014-07-02 /pmc/articles/PMC4091274/ /pubmed/24937681 http://dx.doi.org/10.1021/ja504296x Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Kou, Kevin G. M.
Le, Diane N.
Dong, Vy M.
Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
title Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
title_full Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
title_fullStr Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
title_full_unstemmed Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
title_short Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
title_sort rh(i)-catalyzed intermolecular hydroacylation: enantioselective cross-coupling of aldehydes and ketoamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4091274/
https://www.ncbi.nlm.nih.gov/pubmed/24937681
http://dx.doi.org/10.1021/ja504296x
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AT ledianen rhicatalyzedintermolecularhydroacylationenantioselectivecrosscouplingofaldehydesandketoamides
AT dongvym rhicatalyzedintermolecularhydroacylationenantioselectivecrosscouplingofaldehydesandketoamides

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