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Updated: Mar 10, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Twisting the ethano-Tröger's base: the bisamide
Raul Pereira1, Lukas Pfeifer2, Jean Fournier3
1Department of Chemistry, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, UK. veronique.gouverneur@chem.ox.ac.uk and Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Zürich, Vladimir-Prelog-Weg-2, 8093 Zürich, Switzerland. cvengros@inorg.chem.ethz.ch.
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.
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