Aza-Henry Reactions on C-Alkyl Substituted Aldimines

The reactivity of C-CH(3) substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse ele...

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Detalles Bibliográficos
Autores principales: Pelagalli, Alessia, Pellacani, Lucio, Scandozza, Elia, Fioravanti, Stefania
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273577/
https://www.ncbi.nlm.nih.gov/pubmed/27271579
http://dx.doi.org/10.3390/molecules21060723
Descripción
Sumario:The reactivity of C-CH(3) substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF(3) aldimines, they gave the aza-Henry addition only when ZrCl(4) was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity.

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