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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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
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author Strumfs, Boriss
Hermane, Jekaterina
Belyakov, Sergey
Sobolevs, Artjoms
Velikijs, Kirils
Uljanovs, Romans
Trapencieris, Peteris
Strumfa, Ilze
author_facet Strumfs, Boriss
Hermane, Jekaterina
Belyakov, Sergey
Sobolevs, Artjoms
Velikijs, Kirils
Uljanovs, Romans
Trapencieris, Peteris
Strumfa, Ilze
author_sort Strumfs, Boriss
collection PubMed
description 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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spelling pubmed-86582692021-12-10 An Easy Route to Aziridine Ketones and Carbinols Strumfs, Boriss Hermane, Jekaterina Belyakov, Sergey Sobolevs, Artjoms Velikijs, Kirils Uljanovs, Romans Trapencieris, Peteris Strumfa, Ilze Int J Mol Sci Article 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. MDPI 2021-12-05 /pmc/articles/PMC8658269/ /pubmed/34884949 http://dx.doi.org/10.3390/ijms222313145 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Strumfs, Boriss
Hermane, Jekaterina
Belyakov, Sergey
Sobolevs, Artjoms
Velikijs, Kirils
Uljanovs, Romans
Trapencieris, Peteris
Strumfa, Ilze
An Easy Route to Aziridine Ketones and Carbinols
title An Easy Route to Aziridine Ketones and Carbinols
title_full An Easy Route to Aziridine Ketones and Carbinols
title_fullStr An Easy Route to Aziridine Ketones and Carbinols
title_full_unstemmed An Easy Route to Aziridine Ketones and Carbinols
title_short An Easy Route to Aziridine Ketones and Carbinols
title_sort easy route to aziridine ketones and carbinols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8658269/
https://www.ncbi.nlm.nih.gov/pubmed/34884949
http://dx.doi.org/10.3390/ijms222313145
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