CAREER: Catalyst-controlled Activation of Oxaziridines

本计画以氧氮杂环丙烷的刘易斯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。刘易斯酸催化是发展氧化转化的一种新方法，将适用于各种氧化剂的研究（例如，二环氧乙烷、过氧酸、高价碘）。从根本上讲，新的氧氮丙啶反应性将被开发，包括高度区域选择性的氨羟基化反应。机理的研究将提供一个更深入的了解独特的电子结构和oxenoid反应性的氧氮杂环丙烷。区域选择性不对称烷烃氧化也将探讨，解决有机合成的长期挑战。沟通技巧的训练将被整合到本科和研究生阶段的化学课程中，包括（1）将学生研讨会的同行评价整合到研究生化学课程中，以及（2）将博客作为高级本科实验室课程的课程。在有机和高分子化学项目的支持下，Tehshik P. Yoon教授，威斯康星州大学化学系的研究人员正在开发适用于复杂有机分子的可控和有效合成的新反应。虽然氧化是能够增加有机化合物中的官能度和分子复杂性的基本类型的反应，但是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性构建氧化转化。Yoon教授和他的学生正在开发一种用于催化广泛类别的氧化反应的一般策略。这些研究正在解决有机合成中长期存在的问题，并有望导致新的和有效的化学合成方法。作为一个全面的战略，以更好地准备研究生和本科生在化学专业的最前沿的职业生涯的一部分，教授尹将整合沟通技巧培训到化学课程，介绍学生研讨会和博客的同行评议作为课程在先进的本科实验室课程。

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.