An easy route to aziridine ketones and carbinols

Boriss Strumfs; Jekaterina Hermane; Sergey Belyakov; Artjoms Sobolevs; Kirils Velikijs; Romans Uljanovs; Peteris Trapencieris; Ilze Strumfa

doi:10.3390/ijms222313145

An easy route to aziridine ketones and carbinols

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

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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.

Original language	English
Article number	13145
Number of pages	10
Journal	International Journal of Molecular Sciences
Volume	22
Issue number	23
DOIs	https://doi.org/10.3390/ijms222313145
Publication status	Published - 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

Access to Document

10.3390/ijms222313145

An Easy Route to Aziridine Ketones and CarbinolsFinal published version, 1.65 MBLicence: CC BY

Cite this

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title = "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.",

keywords = "Aziridines, Carbinols, Ketones, Organolithium reagents, Regioselectivity, Tertiary amides",

author = "Boriss Strumfs and Jekaterina Hermane and Sergey Belyakov and Artjoms Sobolevs and Kirils Velikijs and Romans Uljanovs and Peteris Trapencieris and Ilze Strumfa",

note = "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: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = dec,

day = "5",

doi = "10.3390/ijms222313145",

language = "English",

volume = "22",

journal = "International Journal of Molecular Sciences",

issn = "1661-6596",

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TY - JOUR

T1 - An easy route to aziridine ketones and carbinols

AU - Strumfs, Boriss

AU - Hermane, Jekaterina

AU - Belyakov, Sergey

AU - Sobolevs, Artjoms

AU - Velikijs, Kirils

AU - Uljanovs, Romans

AU - Trapencieris, Peteris

AU - Strumfa, Ilze

N1 - 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.

PY - 2021/12/5

Y1 - 2021/12/5

N2 - 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.

AB - 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.

KW - Aziridines

KW - Carbinols

KW - Ketones

KW - Organolithium reagents

KW - Regioselectivity

KW - Tertiary amides

UR - https://www.scopus.com/pages/publications/85120580986

U2 - 10.3390/ijms222313145

DO - 10.3390/ijms222313145

M3 - Article

AN - SCOPUS:85120580986

SN - 1661-6596

VL - 22

JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

IS - 23

M1 - 13145

ER -

An easy route to aziridine ketones and carbinols

Abstract

Keywords*

Field of Science*

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