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Issue 43, 2016
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Lewis acid catalyzed [3 + 2] annulation of ketenimines with donor–acceptor cyclopropanes: an approach to 2-alkylidenepyrrolidine derivatives

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Abstract

The [3 + 2] annulation reaction of C,C,N-trisubstituted ketenimines with donor–acceptor cyclopropanes bearing aryl, styryl and vinyl substituents at the C2 position, triggered by the Lewis acid Sc(OTf)3, supplies highly substituted pyrrolidines. Activated cyclopropanes fused to naphthalene and [1]benzopyrane nuclei are also suitable substrates in similar transformations, yielding partially saturated benz[g]indoles and [1]benzopyran[4,3-b]pyrroles. An intramolecular version of this ketenimine/cyclopropane [3 + 2] annulation has also been developed leading to the pyrrolo[2,1-a]isoindole framework.

Graphical abstract: Lewis acid catalyzed [3 + 2] annulation of ketenimines with donor–acceptor cyclopropanes: an approach to 2-alkylidenepyrrolidine derivatives

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Publication details

The article was received on 12 Sep 2016, accepted on 10 Oct 2016 and first published on 11 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB02005D
Citation: Org. Biomol. Chem., 2016,14, 10275-10284
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    Lewis acid catalyzed [3 + 2] annulation of ketenimines with donor–acceptor cyclopropanes: an approach to 2-alkylidenepyrrolidine derivatives

    M. Alajarin, A. Egea, R. Orenes and A. Vidal, Org. Biomol. Chem., 2016, 14, 10275
    DOI: 10.1039/C6OB02005D

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