Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction

A synthetically convenient approach for the direct α‐deuteration of amides is reported. This mechanistically unusual process relies on a retro‐ene‐type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation...

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Detalles Bibliográficos
Autores principales: Porte, Vincent, Di Mauro, Giovanni, Schupp, Manuel, Kaiser, Daniel, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756638/
https://www.ncbi.nlm.nih.gov/pubmed/33035360
http://dx.doi.org/10.1002/chem.202004103
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author Porte, Vincent
Di Mauro, Giovanni
Schupp, Manuel
Kaiser, Daniel
Maulide, Nuno
author_facet Porte, Vincent
Di Mauro, Giovanni
Schupp, Manuel
Kaiser, Daniel
Maulide, Nuno
author_sort Porte, Vincent
collection PubMed
description A synthetically convenient approach for the direct α‐deuteration of amides is reported. This mechanistically unusual process relies on a retro‐ene‐type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional‐group tolerance and high deuterium incorporation.
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spelling pubmed-77566382020-12-28 Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction Porte, Vincent Di Mauro, Giovanni Schupp, Manuel Kaiser, Daniel Maulide, Nuno Chemistry Communications A synthetically convenient approach for the direct α‐deuteration of amides is reported. This mechanistically unusual process relies on a retro‐ene‐type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional‐group tolerance and high deuterium incorporation. John Wiley and Sons Inc. 2020-11-17 2020-12-01 /pmc/articles/PMC7756638/ /pubmed/33035360 http://dx.doi.org/10.1002/chem.202004103 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Porte, Vincent
Di Mauro, Giovanni
Schupp, Manuel
Kaiser, Daniel
Maulide, Nuno
Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
title Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
title_full Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
title_fullStr Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
title_full_unstemmed Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
title_short Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
title_sort chemoselective alpha‐deuteration of amides via retro‐ene reaction
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756638/
https://www.ncbi.nlm.nih.gov/pubmed/33035360
http://dx.doi.org/10.1002/chem.202004103
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AT schuppmanuel chemoselectivealphadeuterationofamidesviaretroenereaction
AT kaiserdaniel chemoselectivealphadeuterationofamidesviaretroenereaction
AT maulidenuno chemoselectivealphadeuterationofamidesviaretroenereaction

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