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...

Descripción completa

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
Descripción
Sumario: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.

Ejemplares similares