Copper-Catalyzed 1,3-Aminocyclization of Cyclopropanes as A Rapid Entry to γ-Amino Heterocycles
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. In this thesis, 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.
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Nguyen, Andrew (2023). Copper-Catalyzed 1,3-Aminocyclization of Cyclopropanes as A Rapid Entry to γ-Amino Heterocycles. Master's thesis, Duke University. Retrieved from https://hdl.handle.net/10161/30237.
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