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Issue 3, 2017
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Twisting the ethano-Tröger's base: the bisamide

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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

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Publication details

The article was received on 30 Oct 2016, accepted on 06 Dec 2016 and first published on 06 Dec 2016


Article type: Paper
DOI: 10.1039/C6OB02359B
Citation: Org. Biomol. Chem., 2017,15, 628-633
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    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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