Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents

[Image: see text] We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtained with good diastereocont...

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Autores principales: Klake, Raphael K., Gargaro, Samantha L., Gentry, Skyler L., Elele, Sharon O., Sieber, Joshua D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6781103/
https://www.ncbi.nlm.nih.gov/pubmed/31532684
http://dx.doi.org/10.1021/acs.orglett.9b02973
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author Klake, Raphael K.
Gargaro, Samantha L.
Gentry, Skyler L.
Elele, Sharon O.
Sieber, Joshua D.
author_facet Klake, Raphael K.
Gargaro, Samantha L.
Gentry, Skyler L.
Elele, Sharon O.
Sieber, Joshua D.
author_sort Klake, Raphael K.
collection PubMed
description [Image: see text] We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtained with good diastereocontrol. This methodology allows access to chiral γ-hydroxyaldehyde equivalents that were applied in the synthesis of chiral γ-lactones and 2,5-disubstitued tetrahydrofurans.
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spelling pubmed-67811032019-10-09 Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents Klake, Raphael K. Gargaro, Samantha L. Gentry, Skyler L. Elele, Sharon O. Sieber, Joshua D. Org Lett [Image: see text] We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtained with good diastereocontrol. This methodology allows access to chiral γ-hydroxyaldehyde equivalents that were applied in the synthesis of chiral γ-lactones and 2,5-disubstitued tetrahydrofurans. American Chemical Society 2019-09-18 2019-10-04 /pmc/articles/PMC6781103/ /pubmed/31532684 http://dx.doi.org/10.1021/acs.orglett.9b02973 Text en Copyright © 2019 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 Klake, Raphael K.
Gargaro, Samantha L.
Gentry, Skyler L.
Elele, Sharon O.
Sieber, Joshua D.
Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
title Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
title_full Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
title_fullStr Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
title_full_unstemmed Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
title_short Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
title_sort development of a strategy for linear-selective cu-catalyzed reductive coupling of ketones and allenes for the synthesis of chiral γ-hydroxyaldehyde equivalents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6781103/
https://www.ncbi.nlm.nih.gov/pubmed/31532684
http://dx.doi.org/10.1021/acs.orglett.9b02973
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