Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates
Alexandre F. Trindade, Emily L. Faulkner, Andrew G. Leach, Adam Nelson, Stephen P. Marsden
Abstract
A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment.
Topics & Concepts
RegioselectivityChemistryHalideCyclic aminesAlkylAmine gas treatingCombinatorial chemistryElaborationFragment (logic)ElectrochemistryCatalysisOrganic chemistryComputer scienceProgramming languagePhilosophyPhysical chemistryElectrodeHumanitiesRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions