Issue 3, 2017

Twisting the ethano-Tröger's base: the bisamide

Abstract

The typically planar amide when incorporated into bicyclic systems can undergo a significant distortion from planarity resulting in physical properties and reactivity that deviate from classical amide behaviour. Herein, we report a succinct protocol that utilises potassium permanganate to selectively α-oxygenate the benzylic position of ethano-Tröger's base derivatives to yield a new class of twisted bisamides. Additionally, we report the first synthesis of an ethano-Tröger's base derivative bearing substituents in the positions ortho to the nitrogen atoms.

Graphical abstract: Twisting the ethano-Tröger's base: the bisamide

Supplementary files

Article information

Article type
Paper
Submitted
30 Nhl 2016
Accepted
06 N’w 2016
First published
06 N’w 2016

Org. Biomol. Chem., 2017,15, 628-633

Twisting the ethano-Tröger's base: the bisamide

R. Pereira, L. Pfeifer, J. Fournier, V. Gouverneur and J. Cvengroš, Org. Biomol. Chem., 2017, 15, 628 DOI: 10.1039/C6OB02359B

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