CAREER: Annulation Reactions of a-Substituted Allylsilanes

职业：α-取代的烯丙基硅烷的成环反应

• 批准号: 9701622
• 负责人: Keith Woerpel
• 金额: $ 28.89万
• 依托单位: University of California-Irvine
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1997
• 资助国家: 美国
• 起止时间: 1997-05-01 至 2001-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9701622&HistoricalAwards=false
• 关键词: CAREER; Annulation; Reactions; Substituted; Allylsilanes

Professor Woerpel's research focuses on the development of new methodologies for the construction of carbocyclic and heterocyclic compounds through the (3+2) annulation reactions of functionalized allylsilanes. Use of allylsilanes with strategically-placed electron-donating substituents permits rapid 1,2-silyl migration in the initially formed beta-silyl carbocations, leading to more stable carbocations which then undergo annulation with a variety of reactive functionalities. In addition to providing synthetic access to a variety of cyclic structures, these studies also permit the assessment of the role of electronic factors in these annulation reactions. Portions of the research program are particularly designed to encourage participation by undergraduate research students. Professor Woerpel will also examine the effectiveness of new pedagogical tools for improving student comprehension of organic chemistry, focusing on three central themes, stereochemistry, conformational analysis and inductive effects in determining acidity. With this CAREER award, the Synthetic Organic Program supports the research and educational activities of Professor Keith A. Woerpel of the Department of Chemistry at the University of California, Irvine. Professor Woerpel's research efforts are focused on the development of new approaches for the synthesis of cyclic compounds. These studies, exploiting unique reactions of silicon-containing molecules, promise access to a variety of carbocyclic (containing only carbon) and heterocyclic compounds (containing elements such as nitrogen in addition to carbon). Such cyclic structures form the basis of numerous pharmaceutical compounds and other important products. Professor Woerpel's educational activities include the involvement of undergraduates, recruited both from his home campus and through outreach programs, in his research program. Professor Woerpel will also incorporate new laboratory- and computer-based approaches and implement a learning cycle approach to the teaching of undergraduate organic chemistry.

Woerpel教授的研究重点是通过功能化烯丙基硅烷的（3+2）环化反应，开发构建碳环和杂环化合物的新方法。使用烯丙基硅烷和战略性位置的给电子取代基允许1,2-硅基在最初形成的β -硅基碳正离子中快速迁移，导致更稳定的碳正离子，然后通过各种反应官能团进行环化。除了提供各种环结构的合成途径外，这些研究还允许评估电子因素在这些环化反应中的作用。研究项目的部分内容是专门为鼓励本科生参与而设计的。Woerpel教授还将研究新的教学工具在提高学生对有机化学的理解方面的有效性，重点关注三个中心主题：立体化学、构象分析和确定酸度的归纳效应。通过这个职业奖，合成有机项目支持加州大学欧文分校化学系Keith A. Woerpel教授的研究和教育活动。Woerpel教授的研究重点是开发合成环状化合物的新方法。这些研究利用了含硅分子的独特反应，有望获得各种碳环（仅含碳）和杂环化合物（除碳外还含有氮等元素）。这种环状结构构成了许多药物化合物和其他重要产品的基础。Woerpel教授的教育活动包括让本科生参与到他的研究项目中来，这些本科生既从他的家乡校园招募，也通过外展项目招募。Woerpel教授还将采用新的实验室和计算机为基础的方法，并在本科有机化学教学中实施学习循环方法。