Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
Vincent Porte, Giovanni Di Mauro, Manuel Schupp, Daniel Kaiser, Nuno Maulide
Abstract
A synthetically convenient approach for the direct α-deuteration of amides is reported. This mechanistically unusual process relies on a retro-ene-type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional-group tolerance and high deuterium incorporation.
Topics & Concepts
ElectrophileAmideDeuteriumChemistryEne reactionSulfoxideFunctional groupAlpha (finance)Combinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisConstruct validityPhysicsMedicinePolymerPatient satisfactionQuantum mechanicsNursingChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisAdvanced Synthetic Organic Chemistry