New Synthetic Opportunities with N-Alkenylnitrones and N,O-Dialkenylhydroxylamines

美国国家科学基金会化学部化学合成项目通过该奖项支持伊利诺伊大学芝加哥分校（UIC）劳拉·l·安德森教授的研究，以开发构建分子的新方法，以帮助满足社会对新药和新材料的需求。安德森教授与研究生和本科生合作，设计一种名为硝基酮的反应性分子，作为廉价、易得的试剂和复杂的增值化合物之间的关键。这些硝基化合物的关键是转向新的化学键结构。正在确定健壮的路线，以容易地生成关键中间体。这种方法为制药和农业应用提供了新的理想化合物的例子。这项工作的广泛影响来自于新反应产生的化合物，以及确定的新策略和基本反应模式。该项目的教育方面旨在培养有抱负的化学家在研究生和本科水平，以及高中生参加这个项目在夏天。UIC是一个为少数族裔服务的机构，这个项目的额外社会效益包括招收和参与各级代表性不足的学生。Anderson教授和她的学生设计了共轭硝基酮中间体的聚合合成路线和这些中间体的发散立体控制应用，以合成新的杂环。该项目的总体目标是将两种简单的起始材料结合起来，以获得新的反应性中间体，然后调整这些中间体的反应性，通过少量步骤制备一系列增值产品。共轭nitroone中间体的反应性目标包括确定如何控制不对称合成氮杂啶的电环化反应的立体选择性，以及设计指导级联过程合成螺旋环吡咯啉的方法。改善获得共轭硝基酮中间体的目的涉及识别和固定肟的Chan-Lam反应中的障碍。由于确定了基本的反应模式和合成策略，以及通过获得新的杂环化合物而扩大了化学空间，这些活动在更大范围内产生了影响。教育目标是通过培养一群研究生、本科生和高中生进行分析性思考，磨练他们解决问题的能力，并获得STEM学科的实践经验来实现的。代表性不足的群体的参与通过推进多样性进一步为化学的未来提供更好的服务。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Laura L. Anderson at the University of Illinois at Chicago (UIC) to develop new ways to construct molecules to help meet society's demands for new drugs and new materials. Professor Anderson works with graduate and undergraduate students designing ways to use a reactive molecule called a nitrone as the lynchpin between cheap, readily-accessible reagents and complicated value-added compounds. These nitrone lynchpins are tuned towards new chemical bond construction. Robust routes are being determined to easily generate key intermediates. This approach provides access to new examples of desirable compounds for pharmaceutical and agricultural applications. The broader impact of this work results from both the compounds generated from the new reactions, as well as the new strategies and fundamental reactivity patterns that are identified. Educational aspects of the project are aimed towards training aspiring chemists at the graduate and undergraduate level, as well as high school students that participate in the project over the summer. UIC is a minority serving institution and additional societal benefits of this program include the recruitment and participation of under-represented students at all levels.Professor Anderson and her students design convergent synthetic routes to conjugated nitrone intermediates and divergent stereocontrolled applications of these intermediates for the synthesis of novel heterocycles. The overarching goal of this program is to couple two simple starting materials to access novel reactive intermediates and then to tune the reactivity of these intermediates to prepare an array of value-added products in a small number of steps. Reactivity goals for the conjugated nitrone intermediates include determining how to control the stereoselectivity of an electrocyclization reaction for the asymmetric synthesis of azetidines and designing ways to direct a cascade process towards the synthesis of spirocyclic pyrrolines. The aim of improving access to conjugated nitrone intermediates involves identifying and fixing road blocks in the Chan-Lam reactions of oximes. These activities provide impact on a broader scale due to the fundamental reactivity patterns and synthetic strategies that are identified, as well as the expansion of chemical space that is achieved through access to new heterocyclic compounds. Educational goals are achieved by training a group of graduate, undergraduate, and high school students to think analytically, hone their problem-solving skills, and have hands-on experience with a STEM discipline. The involvement of underrepresented groups further serves to better the future of chemistry through advancing diversity.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.