title: 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.
authors.affiliation: Department 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.
authors.forename: Raul
authors.initials: R
authors.lastname: Pereira
authors.affiliation: Department of Chemistry, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, UK. veronique.gouverneur@chem.ox.ac.uk.
authors.forename: Lukas
authors.initials: L
authors.lastname: Pfeifer
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Zürich, Vladimir-Prelog-Weg-2, 8093 Zürich, Switzerland. cvengros@inorg.chem.ethz.ch.
authors.forename: Jean
authors.initials: J
authors.lastname: Fournier
authors.affiliation: Department of Chemistry, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, UK. veronique.gouverneur@chem.ox.ac.uk.
authors.forename: Véronique
authors.initials: V
authors.lastname: Gouverneur
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Zürich, Vladimir-Prelog-Weg-2, 8093 Zürich, Switzerland. cvengros@inorg.chem.ethz.ch.
authors.forename: Ján
authors.identifier: http://orcid.org/0000-0002-8048-7933
authors.initials: J
authors.lastname: Cvengroš