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Twisting the ethano-Tröger's Base: The Bisamide

Raul Pereira, Lukas Pfeifer, Jean Fournier, Véronique Gouverneur, Ján Cvengroš

Org Biomol Chem. 2017 Jan 18;15(3):628-633.

PMID: 27966723

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP21451741 (+)-Tröger's base (+)-Tröger's base 21451-74-1 Price
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