Publication: Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3+2] annulations of ketenimines with donor-acceptor oxiranes and aziridines
Authors
Alajarín, Mateo ; Banon, David ; Egea, Adrian ; Marin-Luna, Marta ; Orenes, Raul A. ; Vidal, Angel
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Publisher
Royal Society of Chemistry
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DOI
10.1039/C8QO00255J
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info:eu-repo/semantics/article
Description
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.
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Citation
Org. Chem. Front., 2018, 5, 2020-2029.
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