Dissertation/Thesis Abstract

Copper(ii) catalyzed enantioselective intra/intermolecular diamination and hydroamination of alkenes
by Turnpenny, Benjamin William, Ph.D., State University of New York at Buffalo, 2014, 177; 3613109
Abstract (Summary)

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.

Indexing (document details)
Advisor: Chemler, Sherry R.
Commitee: Diver, Steven T., Rzayev, Javid, Watson, David F.
School: State University of New York at Buffalo
Department: Chemistry
School Location: United States -- New York
Source: DAI-B 75/06(E), Dissertation Abstracts International
Source Type: DISSERTATION
Subjects: Organic chemistry
Keywords: Chemler, Copper, Diamination, Hydroamination
Publication Number: 3613109
ISBN: 9781303752308
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