Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides

[Image: see text] A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung viaN-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolate...

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Autores principales: Kaiser, Daniel, Teskey, Christopher J., Adler, Pauline, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5691317/
https://www.ncbi.nlm.nih.gov/pubmed/29099184
http://dx.doi.org/10.1021/jacs.7b08813
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author Kaiser, Daniel
Teskey, Christopher J.
Adler, Pauline
Maulide, Nuno
author_facet Kaiser, Daniel
Teskey, Christopher J.
Adler, Pauline
Maulide, Nuno
author_sort Kaiser, Daniel
collection PubMed
description [Image: see text] A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung viaN-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolates. The method conveys broad functional group tolerance on both components, does not suffer from formation of homocoupling byproducts and avoids the use of transition metal catalysts.
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spelling pubmed-56913172017-11-18 Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides Kaiser, Daniel Teskey, Christopher J. Adler, Pauline Maulide, Nuno J Am Chem Soc [Image: see text] A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung viaN-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolates. The method conveys broad functional group tolerance on both components, does not suffer from formation of homocoupling byproducts and avoids the use of transition metal catalysts. American Chemical Society 2017-11-03 2017-11-15 /pmc/articles/PMC5691317/ /pubmed/29099184 http://dx.doi.org/10.1021/jacs.7b08813 Text en Copyright © 2017 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 Kaiser, Daniel
Teskey, Christopher J.
Adler, Pauline
Maulide, Nuno
Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
title Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
title_full Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
title_fullStr Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
title_full_unstemmed Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
title_short Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
title_sort chemoselective intermolecular cross-enolate-type coupling of amides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5691317/
https://www.ncbi.nlm.nih.gov/pubmed/29099184
http://dx.doi.org/10.1021/jacs.7b08813
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AT maulidenuno chemoselectiveintermolecularcrossenolatetypecouplingofamides

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