Issue 18, 2006

Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

Abstract

Readily prepared 2-alkyl-2-azidopropylcycloalkyl-1,3-diones undergo intramolecular Schmidt rearrangement with a range of hard Lewis acids, leading to indolizidinediones and pyrroloazepinediones. Chiral aluminium-based Lewis acids could also be used to mediate this symmetry-breaking transformation, but no significant asymmetric induction was observed.

Graphical abstract: Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

Supplementary files

Article information

Article type
Paper
Submitted
21 Jun 2006
Accepted
12 Jul 2006
First published
03 Aug 2006

Org. Biomol. Chem., 2006,4, 3498-3504

Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

D. Lertpibulpanya and S. P. Marsden, Org. Biomol. Chem., 2006, 4, 3498 DOI: 10.1039/B608801E

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