Sulfonium Ylides to Quaternary Substituted Indolines

本项目致力于开发具有C(3)四元取代的吲哚化合物的非对映和对映体选择性方法。有效地生成这些物种的化学转化包括2-硫代吲哚与通过Rh(II)络合物与重氮乙酸乙烯酯反应生成的乙烯基卡宾的偶联。这些研究将使我们更好地理解这一反应的范围，更好地从根本上理解硫叶立德的化学，并增加我们对吲哚反应活性的理解。虽然这一应用并不集中在特定的目标分子上，但从硫叶立德化学中得到的产物将经历各种化学转化，导致合成一系列不同的结构，其中一些存在于生物活性目标中。在有机和高分子化学计划的支持下，犹他大学化学系的乔恩·D·雷尼尔教授正在研究独特的金属介导的反应，这些反应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，Rainier教授和他的学生正在开发对不寻常和活性有机物种的结构和反应性的深入基本了解，以及一套帮助合成有机分子的新工具。对通过化学反应和反应性进行化学合成的基本了解将对一些重要领域产生广泛影响。其中最明显的是与新药和新材料的开发有关的那些。不太明显的是生物和环境科学，在这些科学中，化学反应起着核心作用。此外，这一化学合成计划将通过培养在其独立职业生涯中将在化学、生物技术和制药行业以及/或在学术界发挥重要作用的科学家而有益于社会。

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.