Versatile Rh-catalyzed C-H bond functionalization methods will be presented for the rapid assembly of drug relevant amines and heterocycles, including architecturally complex structures from simple and readily available inputs. Transformations based upon Rh(III) catalysis include the convergent asymmetric synthesis of amines and cascade sequences to heterocycles found in pharmaceuticals such as pyrroles, furans, indazoles, isoindolinones, phenazines, acridines and pyridines. Practical and convergent routes to substituted 1,2-dihydropyridines by a Rh(I)-catalyzed C-H bond alkenylation/electrocyclization sequence will also be described. Regio- and stereoselective elaboration of the 1,2-dihydropyridines then provides rapid entry to densely substituted piperidines, tropanes, isoquinuclidines, and even more complex multicyclic nitrogen heterocycles. The scope and mechanisms for these new methods will be provided. Their utility will also be illustrated by short and efficient syntheses of important pharmaceutical agents.

C-H bond functionalization cascades for the synthesis of complex heterocycles

249th National Meeting (2015)

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