Sulfonium Ylides to Quaternary Substituted Indolines

锍叶立德转化为季取代二氢吲哚

• 批准号: 0650405
• 负责人: Jon Rainier
• 金额: $ 40.8万
• 依托单位: University of Utah
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2007
• 资助国家: 美国
• 起止时间: 2007-08-15 至 2010-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0650405&HistoricalAwards=false
• 关键词: Sulfonium; Ylides; Quaternary; Substituted; Indolines

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.

本计画致力于发展非对映体及对映体选择性的方法来合成在C（3）位有季取代的二氢吲哚。使这些物种的有效生成的化学转化涉及的2-硫代吲哚与乙烯基卡宾通过Rh（II）配合物与乙烯基重氮乙酸酯的反应产生的耦合。这些研究将导致更好地了解这一反应的范围，更好地了解锍叶立德的化学基础，以及增加我们对吲哚反应性的理解。虽然这种应用程序并不集中在特定的目标分子，从锍叶立德化学的产品将进行各种化学转化，导致合成的各种各样的架构，其中一些是目前在生物活性的目标。犹他州大学化学系的Rainier正在研究独特的金属介导的反应，这种反应可以快速有效地提供与生物活性化合物合成相关的复杂结构。通过这些研究，Rainier教授和他的学生们正在对不寻常和反应性有机物种的结构和反应性进行深入的基本了解，并开发出一套有助于有机分子合成的新工具。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开发新药物和材料有关的问题。在生物和环境科学中，化学反应性起着核心作用，这一点不太明显。此外，该化学合成计划将通过培养科学家对社会有益，这些科学家将在化学，生物技术和制药行业和/或学术界等领域的独立职业生涯中发挥重要作用。