An easy route to aziridine ketones and carbinols

Boriss Strumfs, Jekaterina Hermane, Sergey Belyakov, Artjoms Sobolevs, Kirils Velikijs, Romans Uljanovs, Peteris Trapencieris, Ilze Strumfa (Coresponding Author)

Research output: Contribution to journalArticlepeer-review

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 (−78C) 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.

Original languageEnglish
Article number13145
Number of pages10
JournalInternational Journal of Molecular Sciences
Volume22
Issue number23
DOIs
Publication statusPublished - 5 Dec 2021

Keywords*

  • Aziridines
  • Carbinols
  • Ketones
  • Organolithium reagents
  • Regioselectivity
  • Tertiary amides

Field of Science*

  • 1.4 Chemical sciences

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

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