Issue 43, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Sep 2016
Accepted
10 Oct 2016
First published
11 Oct 2016

Org. Biomol. Chem., 2016,14, 10275-10284

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements