Copper-Catalyzed 1,3-Aminocyclization of Cyclopropanes as A Rapid Entry to γ-Amino Heterocycles

Andrew Nguyen, M.S. Candidate Qiu Wang Ph.D., Advisor Abstract: Heterocycles represent an important class of motifs found in many bioactive molecules, pharmaceuticals, and agrochemicals. The ability to rapidly construct a diverse set of these compounds remains an important endeavor in the field of synthetic chemistry. An intramolecular 1,3-difunctionalization of cyclopropanes is reported using a copper-NFSI catalyzed system. Direct oxidation of the substrate by a nitrogen centered radical activates the cyclopropane which then undergoes a ring-opening cascade to produce a variety of lactones, cyclic ethers, pyrrolidines, and oximes containing γ-amino functionalization. Further product derivatization can produce various protected amines and alkyl-sulfonamides.