Switching and Conformational Fixation of Amides Through Proximate Positive Charges.

Angew Chem Int Ed Engl

Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany) http://www.medchem.uni-erlangen.de/heinrichlab/.

Published: August 2015

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.

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http://dx.doi.org/10.1002/anie.201502474DOI Listing

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