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An Easy Route to Aziridine Ketones and Carbinols.

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.

SUBMITTER: Strumfs B

PROVIDER: S-EPMC8658269 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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An Easy Route to Aziridine Ketones and Carbinols.

Strumfs Boriss B Hermane Jekaterina J Belyakov Sergey S Sobolevs Artjoms A Velikijs Kirils K Uljanovs Romans R Trapencieris Peteris P Strumfa Ilze I

International journal of molecular sciences 20211205 23

<i>N,N</i>-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. ...[more]

PMID: 34884949

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