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Issue 2, 2013
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Cycloaddition of tertiary aziridines and carbon dioxide using a recyclable organocatalyst, 1,3-di-tert-butylimidazolium-2-carboxylate: straightforward access to 3-substituted 2-oxazolidones

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Abstract

Imidazolium-2-carboxylates derived from N-heterocyclic carbenes (NHCs) and CO2 serve as efficient catalysts for CO2-carboxylation of tertiary aziridines bearing various substituents such as halogens, ether, olefin, ester, acetal, and nitro groups on the aziridine ring in 2-propanol, leading to 3-substituted-2-oxazolidones in good to excellent yields and with high selectivity. The NHC–CO2 adducts facilitate nucleophilic attack of the CO2 moiety on the aziridines, in which the substituents are intact during the carboxylation. The catalyst is successfully recycled up to five times with no apparent loss in activity.

Graphical abstract: Cycloaddition of tertiary aziridines and carbon dioxide using a recyclable organocatalyst, 1,3-di-tert-butylimidazolium-2-carboxylate: straightforward access to 3-substituted 2-oxazolidones

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Publication details

The article was received on 06 Sep 2012, accepted on 25 Oct 2012 and first published on 25 Oct 2012


Article type: Paper
DOI: 10.1039/C2GC36414J
Citation: Green Chem., 2013,15, 425-430
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    Cycloaddition of tertiary aziridines and carbon dioxide using a recyclable organocatalyst, 1,3-di-tert-butylimidazolium-2-carboxylate: straightforward access to 3-substituted 2-oxazolidones

    A. Ueno, Y. Kayaki and T. Ikariya, Green Chem., 2013, 15, 425
    DOI: 10.1039/C2GC36414J

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