Issue 2, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Sep 2012
Accepted
25 Oct 2012
First published
25 Oct 2012

Green Chem., 2013,15, 425-430

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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