Issue 13, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 Mar 2018
Accepted
09 May 2018
First published
09 May 2018

Org. Chem. Front., 2018,5, 2020-2029

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, 5, 2020 DOI: 10.1039/C8QO00255J

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