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Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3 + 2] annulations of ketenimines with donor–acceptor oxiranes and aziridines

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Abstract

Efficient [3 + 2] annulations of N-aryl-C,C-diphenyl ketenimines with metallo-carbonyl and metallo-azomethine ylides, generated via the respective Yb(OTf)3 and Y(OTf)3 promoted carbon–carbon bond heterolysis of donor–acceptor oxiranes and aziridines, have been accomplished. These reactions proceeded under mild conditions and supplied a general methodology for the regioselective construction of structurally complex oxazolidines and pyrrolidines. Moreover, heating neat mixtures of N-aryl-C,C-diphenyl ketenimines and diethyl aziridine-2,3-dicarboxylates led to imidazolidine derivatives. A computational study concluded in stepwise mechanisms for these [3 + 2] annulations, also shedding light on their regioselectivity, concerning which of the two cumulated double bonds of the ketenimine becomes involved in the reaction with the ylide.

Graphical abstract: Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3 + 2] annulations of ketenimines with donor–acceptor oxiranes and aziridines

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Publication details

The article was received on 08 Mar 2018, accepted on 09 May 2018 and first published on 09 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00255J
Citation: Org. Chem. Front., 2018, Advance Article
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    Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3 + 2] annulations of ketenimines with donor–acceptor oxiranes and aziridines

    M. Alajarin, D. Bañon, A. Egea, M. Marín-Luna, R. Orenes and A. Vidal, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00255J

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