Sulfonium Ylides to Quaternary Substituted Indolines

本项目致力于发展非映对和对映选择性方法来研究在C(3)上具有四元取代的吲哚类化合物。使这些物种有效产生的化学转化涉及到2-硫吲哚与乙烯基类碳化合物的偶联，这些类碳化合物是通过Rh（II）配合物与乙烯基重氮乙酸酯反应产生的。这些研究将使我们更好地了解这一反应的范围，更好地了解磺酰化的基本化学性质，并增加我们对吲哚的反应性的了解。虽然这一应用并不集中在特定的靶分子上，但来自磺酰化化学的产物将受到各种化学转化的影响，从而合成各种各样的结构，其中一些存在于生物活性靶标中。在有机和大分子化学项目的支持下，犹他大学化学系的Jon D. Rainier教授正在研究独特的金属介导反应，这种反应可以快速有效地提供与合成生物活性化合物相关的复杂结构。通过这些研究，雷尼尔教授和他的学生们对不寻常的和活性的有机物质的结构和反应性有了深入的了解，并开发了一套帮助合成有机分子的新工具。通过化学反应和反应性对化学合成的基本理解将对许多重要领域产生广泛的影响。其中最明显的是那些与新药物和新材料的开发有关的。稍微不那么明显的是生物和环境科学，其中化学反应性起着核心作用。此外，这一化学合成计划将有利于社会培养科学家谁将在其独立的职业生涯中发挥重要作用的领域，如化学，生物技术，制药工业，和/或在学术界。

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.