Palladium-Catalyzed Cross-Couplings of 2-Alkylaziridines and Alkenylboronic Acids

Thesis (Master's)--University of Washington, 2016-08

A new method to synthesize substituted homoallylic amines is reported. Homoallylic amines are important structural moieties in natural products and pharmaceutical agents. The reaction couples N-nosyl-2-alkylaziridines with alkenylboronic acids under palladium catalysis. This work examines the role of base and proton donor additive in facilitating formation of the desired product. The reaction has promising yields and appears to have a wide substrate scope. This work expands upon the Michael lab's previous work with cross-couplings of alkyl aziridines and arylboronic acids.