Complexity Control in Enyne Photocycloadditions

有了这个奖项，化学系的化学合成计划资助坦普尔大学化学系的Scott Sieburth教授研究芳环和烯炔之间的光化学环加成反应（又名环加成反应）。乙烯基乙炔类）及其产品的应用。 环加成反应是构建分子的最有效方法之一。 这种新的环加成反应通过将两个四原子组分聚集在一起而组装成一个八元环，这是一个不容易接近的中环。 [4+4]类的环加成反应本身是不寻常的，烯炔用于该反应是前所未有的。 该产品含有应变和高反应性的丙二烯，经历随后的化学反应，包括重排和额外的环加成反应。 总的来说，这种光反应需要简单的组分，并在一个步骤中构建复杂的产物，这些产物富含官能团和立体化学。 为了快速构建有用的新化学结构，将研究反应性丙二烯官能团的捕获，包括分子间和分子内。 更广泛的影响包括培训本科生、研究生和博士后研究人员。 这项工作可能导致具有有用特性的新化学结构，这些结构是使用标准合成转换无法获得的。 此外，使用光而不是化学试剂来诱导反应，本质上是一种“绿色”过程。 这种化学的成功开发将对依赖新型分子及其特性的研究产生广泛的影响，例如制药和农业行业。 此外，该项目还将为学生提供现代有机合成和光化学方面的培训，从本科生到博士后，包括那些来自历史上在科学领域代表性不足的群体的学生。

With this award, the Chemical Synthesis Program of the Chemistry Division is funding Professor Scott Sieburth of the Department of Chemistry at Temple University to study a photochemical cycloaddition reaction between aromatic rings and enynes (a.k.a. vinyl acetylenes) and application of the products. Cycloaddition reactions are among the most powerful ways of building molecules. This new cycloaddition assembles an eight-membered ring, a medium ring that is not easily accessible, by bringing together two four-atom components. The [4+4] class of cycloadditions is itself unusual and use of enynes for this reaction is unprecedented. The product contains a strained and highly reactive allene that undergoes subsequent chemistry, including rearrangements and additional cycloaddition reactions. Overall, this photoreaction takes simple components and builds complex products in a single step that are rich in functional groups and stereochemistry. With a goal of building useful new chemical structures rapidly, trapping of the reactive allene functional group will be studied, both inter- and intramolecularly. The broader impacts involve training undergraduate students, graduate students and postdoctoral researchers. This work could lead to new chemical structures with useful properties, structures that are not accessible using standard synthetic transformations. Moreover, the use of light to induce reactions, instead of chemical reagents, is an intrinsically "green" process. Successful development of this chemistry will have a broad impact on research that relies on novel molecules and their properties, such as the pharmaceutical and agricultural industries. In addition, this project will provide training in both modern organic synthesis and photochemistry for students, from undergraduate to post-doctoral, including those from groups historically underrepresented in the sciences.