An easy route to aziridine ketones and carbinols
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Date
2021-12-05
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Abstract
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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Funding Information: Funding: This research was funded by the European Regional Development Fund, project No. 1.1.1.2/VIAA/1/16/242. The APC was funded by Riga Stradins University, Riga, Latvia. Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
Keywords
Aziridines, Carbinols, Ketones, Organolithium reagents, Regioselectivity, Tertiary amides, 1.4 Chemical sciences, 1.1. Scientific article indexed in Web of Science and/or Scopus database, Catalysis, Molecular Biology, Spectroscopy, Computer Science Applications, Physical and Theoretical Chemistry, Organic Chemistry, Inorganic Chemistry
Citation
Strumfs, B, Hermane, J, Belyakov, S, Sobolevs, A, Velikijs, K, Uljanovs, R, Trapencieris, P & Strumfa, I 2021, 'An easy route to aziridine ketones and carbinols', International Journal of Molecular Sciences, vol. 22, no. 23, 13145. https://doi.org/10.3390/ijms222313145