Leveraging Electron‐Deficient Iminium Intermediates in a General Synthesis of Valuable Amines
Che‐Sheng Hsu, Carlos R. Gonçalves, Veronica Tona, Amandine Pons, Marcel Kaiser, Nuno Maulide
Abstract
The development of reactions converting alkenes and alkynes into valuable building blocks remains one of the main goals of synthetic chemistry. Herein, we present the leveraging of highly electron-deficient iminium ions, rare and fleeting intermediates, into a general amine synthesis. This enables the preparation of amines bearing e.g. valuable α-trifluoromethyl moieties under mild conditions. This broad concept is highlighted by the late-stage amination of quinine into a biologically interesting new analogue.
Topics & Concepts
IminiumAminationChemistryAmine gas treatingCombinatorial chemistryTrifluoromethylReductive aminationIonOrganic chemistryCatalysisAlkylFluorine in Organic ChemistrySynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms