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 10 2016
Accepted
06 12 2016
First published
06 12 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

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