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Updated: Sep 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Synthesis of Aminocyclopropanes by Redox-Neutral Aminoalkylation
Gwyndaf A Oliver1, Konstantin Günther1,2,3, Chiara Sebastianelli-Schoditsch4
1Institute of Organic Chemistry, University of Vienna, Vienna, Austria.
Abstract:
A redox-neutral hydroaminoalkylation strategy has been developed for the synthesis of 1,1-disubstituted aminocyclopropanes from alkenes and alkynes. Through simple solvolysis activation, the reaction of an easily accessible, bench-stable hemiaminal precursor allows excellent yields of the target products at ambient temperature. The approach presented herein has a substrate tolerance that is orthogonal to classical aminocyclopropane syntheses, and its deployment for the preparation of bioisosteres of pharmacologically active gem-α-dimethylamines resulted in improved biological properties.
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