Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
Benjamin T. Jones, Javier Garcı́a-Cárceles, Lewis Caiger, Ian R. Hazelden, Richard J. Lewis, Thomas Langer, John F. Bower
Abstract
-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Topics & Concepts
ChemistryArylSurface modificationHeck reactionStereochemistryCombinatorial chemistryOrganic chemistryAlkylPhysical chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsOxidative Organic Chemistry Reactions