CAREER: Annulation Reactions of a-Substituted Allylsilanes

沃佩尔教授的研究集中于开发新的方法，通过官能化的烯丙基硅烷的(32)环化反应来构建碳环和杂环化合物。烯丙基硅烷与战略放置的给电子取代基的使用允许1，2-硅基在最初形成的β-硅基碳正离子中快速迁移，从而产生更稳定的碳正离子，然后通过各种反应官能团进行环化。除了提供各种环状结构的合成途径外，这些研究还允许评估电子因素在这些环化反应中的作用。研究计划的部分内容是特别为鼓励本科生参与设计的。沃佩尔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，重点放在三个中心主题上，即立体化学、构象分析和确定酸度的诱导效应。通过这一职业奖，合成有机项目支持加州大学欧文分校化学系基思·A·沃佩尔教授的研究和教育活动。沃尔佩尔教授的研究重点是开发合成环状化合物的新方法。这些研究利用含硅分子的独特反应，有望获得各种碳环(只含碳)和杂环化合物(除碳外还含有氮等元素)。这种环结构形成了许多药物化合物和其他重要产品的基础。沃佩尔教授的教育活动包括让本科生参与他的研究项目，这些本科生既是从他的家乡校园招募的，也是通过外展项目招募的。沃佩尔教授还将结合基于实验室和计算机的新方法，并在本科生有机化学教学中实施学习循环方法。

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.