An Easy Route to Aziridine Ketones and Carbinols

N,N-Dimethylaziridine-2-carboxamides react with organolithium reagents yielding 2-aziridinylketones. The reaction with one equivalent of organolithium compound is selective to amide carbonyl at a low (−78 °C) temperature. These ketones, in reaction with organolithium reagents, give symmetrical and u...

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Detalles Bibliográficos
Autores principales: Strumfs, Boriss, Hermane, Jekaterina, Belyakov, Sergey, Sobolevs, Artjoms, Velikijs, Kirils, Uljanovs, Romans, Trapencieris, Peteris, Strumfa, Ilze
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8658269/
https://www.ncbi.nlm.nih.gov/pubmed/34884949
http://dx.doi.org/10.3390/ijms222313145
Descripción
Sumario:N,N-Dimethylaziridine-2-carboxamides react with organolithium reagents yielding 2-aziridinylketones. The reaction with one equivalent of organolithium compound is selective to amide carbonyl at a low (−78 °C) temperature. These ketones, in reaction with organolithium reagents, give symmetrical and unsymmetrical aziridinyl carbinols. The usage of excess phenyllithium may serve as a special N-Boc-protecting group cleavage method for acid-sensitive substrates.

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