title: Switching and Conformational Fixation of Amides Through Proximate Positive Charges.
abstract: Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.
authors.affiliation: Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany) http://www.medchem.uni-erlangen.de/heinrichlab/
authors.forename: Amelie L
authors.initials: AL
authors.lastname: Bartuschat
authors.affiliation: Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany) http://www.medchem.uni-erlangen.de/heinrichlab/
authors.forename: Karina
authors.initials: K
authors.lastname: Wicht
authors.affiliation: Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany) http://www.medchem.uni-erlangen.de/heinrichlab/. Markus.Heinrich@fau.de.
authors.forename: Markus R
authors.initials: MR
authors.lastname: Heinrich
keywords: amide bond; ammonium ions; conformation; proline; rotamers