Copper(ii) catalyzed enantioselective intra/intermolecular diamination and hydroamination of alkenes
Turnpenny, Benjamin William
MetadataShow full item record
Nitrogen heterocycles are ubiquitous in bioactive compounds. The development of new chemical methods which provide an efficient and concise synthesis of these molecules is a prevalent topic. The research described herein examines the formation of nitrogen heterocycles utilizing copper(II)-catalyzed difunctionalization reactions of alkenes. In Chapter I, a copper-catalyzed enantioselective intra/intermolecular alkene diamination is described. This reaction couples various γ-alkenyl sulfonamides with various external sulfonamides via a tandem cyclization/coupling sequence and enables formation of chiral 2-methylamino indolines and pyrrolidines. Chapter II is focused on the copper-catalyzed enantioselective diamination/cyclization of N -sulfonyl-2-allylanilines to synthesize chiral 2-methylindolines. The method was expanded to include various substitutions on the aniline ring of the substrate, and provided hydroamination products with up to 90% ee.