Sulfonium Ylides to Quaternary Substituted Indolines

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This project addresses the development of diastereo- and enantioselective approaches to indolines having quaternary substitution at C(3). The chemical transformation enabling the efficient generation of these species involves the coupling of 2-thioindoles with vinyl carbenoids generated through the reaction of Rh(II) complexes with vinyl diazoacetates. These studies will lead to both a better understanding of the scope of this reaction and a better fundamental understanding of the chemistry of sulfonium ylides as well as adding to our understanding of the reactivity of indoles. Although this application is not focused on specific target molecules, the products from the sulfonium ylide chemistry will be subjected to a variety of chemical transformations, leading to the synthesis of a diverse array of architectures, some of which are present in bioactive targets.With the support of the Organic and Macromolecular Chemistry Program, Professor Jon D. Rainier, of the Department of Chemistry at the University of Utah, is studying unique metal-mediated reactions that rapidly and efficiently afford complex structures relevant to the synthesis of biologically active compounds. Through these studies, Professor Rainier and his students are developing both an in-depth fundamental understanding of the structure and reactivity of unusual and reactive organic species and a set of new tools aiding in the synthesis of organic molecules. A fundamental understanding of chemical synthesis through chemical reactions and reactivity will have a broad impact on a number of important areas. The most obvious of these are those that are associated with the development of new medicines and materials. Somewhat less obvious are the biological and environmental sciences where chemical reactivity plays a central role. In addition, this chemical synthesis program will be beneficial to society by training scientists who will play important roles during their independent careers in areas such as the chemical, biotech, and pharmaceutical industries, and/or in academia.