Issue 77, 2016

Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction

Abstract

A diastereoselective, DABCO-catalyzed reaction of isatin-derived ketimines with allenoates is described. Exploiting the stereodirecting effect of the bulky tert-butanesulfinyl chiral auxiliary, the method provides an efficient access to single diastereoisomers of unprecedented spirocyclic oxindoles, bearing a 4-methyleneazetidine ring at the spiro junction. The versatility of the method is fully demonstrated by further transformations including the conversion to relevant spirocyclic oxindolo-β-lactams.

Graphical abstract: Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction

Supplementary files

Article information

Article type
Communication
Submitted
15 júl. 2016
Accepted
25 ágú. 2016
First published
26 ágú. 2016
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2016,52, 11575-11578

Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction

G. Rainoldi, M. Faltracco, L. Lo Presti, A. Silvani and G. Lesma, Chem. Commun., 2016, 52, 11575 DOI: 10.1039/C6CC05838H

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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