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

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 14, Issue: 43, Page: 10275-10284
2016
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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), 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.

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