CAREER: Catalyst-controlled Activation of Oxaziridines

该项目致力于研究恶氮杂环类化合物的Lewis酸活化，作为发现一系列新的立体选择性催化氧化方法的统一平台。Lewis酸催化是发展氧化转化的一种新方法，将适用于研究各种氧化剂(如二氧六环、过氧酸、高价碘)。从根本上讲，将开发新的恶氮杂环丙烷反应性，包括高度区域选择性的氨基羟基化反应。机理研究将为了解恶氮杂环类化合物独特的电子结构和恶烯反应活性提供更深入的认识。还将探索区域选择性不对称烷烃氧化，以解决有机合成中的长期挑战。沟通技能培训将通过(1)将学生研讨会的同行评估整合到研究生化学课程中，以及(2)在高级本科实验室课程中引入博客作为课程作业，将沟通技能培训整合到本科生和研究生的化学课程中。在有机化学和高分子化学项目的这一职业奖项的支持下，威斯康星大学化学系的特赫希克·P·杨教授正在开发适用于复杂有机分子的受控和高效合成的新反应。尽管氧化反应是一类基本的反应，能够增加有机化合物的官能度和分子复杂性，但使用已知的对映选择性催化方法只能实现有限数量的复杂氧化转化。尹教授和他的学生正在开发一种广泛的氧化反应类催化的总体策略。这些研究正在解决有机合成中长期存在的问题，并有望带来新的有效的化学合成方法。作为一项更好地为研究生和本科生在化学专业前沿的职业生涯做好准备的综合战略的一部分，尹教授将把沟通技能培训纳入化学课程，将学生研讨会和博客的同行评议作为高级本科实验室课程的课程。

This project addresses the Lewis acid activation of oxaziridines as a unified platform for the discovery of a range of new stereoselective catalytic oxidative methods. Lewis acid catalysis is a new approach to the development of oxidative transformations and will be applicable to the study of a variety of oxidants (e.g., dioxiranes, peroxyacids, hypervalent iodine). Fundamentally new oxaziridine reactivity will be developed, including highly regioselective aminohydroxylation reactions. Mechanistic studies will provide a deeper insight into the unique electronic structure and oxenoid reactivity of oxaziridines. Regioselective asymmetric alkane oxidation will also be explored, addressing a long-standing challenge in organic synthesis. Communication skills training will be integrated into the chemistry curriculum at both the undergraduate and graduate level by (1) integrating peer evaluation of our student seminars into the graduate chemistry curriculum, and (2) introducing blogs as coursework in an advanced undergraduate laboratory course.With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Tehshik P. Yoon, of the Department of Chemistry at the University of Wisconsin, is developing new reactions applicable to the controlled and efficient synthesis of complex organic molecules. Although oxidations are a fundamental class of reactions capable of increasing functionality and molecular complexity in organic compounds, only a limited number of complexity-building oxidative transformations can be achieved using known methods of enantioselective catalysis. Professor Yoon and his students are developing a general strategy for the catalysis of broad classes of oxidation reactions. These studies are addressing long-standing problems in organic synthesis and are expected to lead to new and efficient methods for chemical synthesis. As part of a comprehensive strategy to better prepare both graduate and undergraduate students for careers at the forefront of the chemistry professions, Professor Yoon will integrate communication skills training into the chemistry curriculum, introducing peer review of student seminars and blogs as coursework in an advanced undergraduate laboratory course.