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.
|Advisor:||Chemler, Sherry R.|
|Commitee:||Diver, Steven T., Rzayev, Javid, Watson, David F.|
|School:||State University of New York at Buffalo|
|School Location:||United States -- New York|
|Source:||DAI-B 75/06(E), Dissertation Abstracts International|
|Keywords:||Chemler, Copper, Diamination, Hydroamination|
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