CAREER: New Pericyclic Methodologies for the Convergent Synthesis of Complex Ring Systems

在化学系化学合成计划的支持下，佐治亚大学的克里斯托弗·牛顿正在设计新的分子“积木”，以提高分子加成反应的反应性和多功能性。这些加成反应能够通过连接两个更简单的片段来快速构建复杂的有机分子，这项研究的目的是解决该领域长期存在的限制其应用的挑战。目标反应预计将导致一套不同的包含碳、氧和氮原子的环状结构。还将对支撑这些转变的机制进行详细研究，以帮助促进未来的发现。这项研究的结果将产生广泛的科学和社会影响，包括在制药、材料和农化行业。这项资助的研究还将支持对不同群体的本科生和研究生进行最先进的化学技术培训，帮助加强美国未来的STEM(科学、技术、工程和数学)劳动力。此外，牛顿博士和他的团队将致力于创建和传播免费、开放的化学教育工具，以减少障碍并扩大STEM的参与度。最后，该奖项将支持一个与当地高中教师合作的推广计划，为大雅典，GA社区提供实践实验室经验和职业指导。在克里斯托弗·牛顿的指导下，该研究计划的总体目标是开发新的、基于周环的策略，用于高价值复杂环系的聚合合成。这项研究旨在通过使用非典型的、高氧化态的积木来调整环加成反应的反应性，包括历史悠久的Diels-Alder反应。与目前最先进的方法相比，这些新片段的加入导致了产品的复杂性和功能性的增加。该研究计划有三个不同的目标：(I)开发第一个交叉偶联活性Diels-Alder双烯的通用家族，(Ii)一步Diels-Alder/环扩展路线，得到7元和8元杂环和碳环基序，以及(Iii)开发一类新型的高活性氮杂双烯化合物。这些努力的成功有望提供大量高度功能化、生物活性的多环分子的有效途径，同时也促进了对反应模式这一重要领域的结构和反应性的基本了解。该奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis program in the Division of Chemistry, Christopher Newton of the University of Georgia is designing novel molecular “building blocks” that improve the reactivity and versatility of molecular addition reactions. These addition reactions enable the rapid construction of complex organic molecules through the joining of two simpler fragments and this research aims to address long-standing challenges in the field that have limited its applications. The targeted reactions are expected to lead to a diverse set of cyclic structures containing carbon, oxygen, and nitrogen atoms. Detailed studies of the mechanisms underpinning these transformations will also be undertaken, helping to facilitate future discoveries. The outcomes of this research stand to have broad scientific and societal impacts including in the pharmaceutical, material, and agrochemical industries. The funded research will also support the training of a diverse body of undergraduate and graduate students in state-of-the-art chemistry techniques, helping to strengthen the future STEM (science, technology, engineering and mathematics) workforce in the United States. In addition, Dr. Newton and his team will work to create and disseminate free, open-access chemistry educational tools to reduce barriers and broaden engagement in STEM. Finally, this award will support an outreach program, in collaboration with local high school teachers, to provide hands-on laboratory experience and career guidance to the greater Athens, GA community.The overarching goal of the research program under the guidance of Christopher Newton is to develop novel, pericyclic-based strategies for the convergent synthesis of high-value complex ring systems. This study aims to tailor the reactivity of cycloaddition reactions, including the venerable Diels-Alder reaction, through the use of atypical, high oxidation state building blocks. The joining of these novel fragments leads to products of increased complexity and functionality when compared to current state-of-the-art approaches. The research plan has three distinct objectives: (i) development of the first general family of cross-coupling active Diels–Alder dienes, (ii) a one-step Diels–Alder/ring expansion route to 7- and 8-membered hetero- and carbocyclic motifs, and (iii) development of a novel, highly reactive class of aza-dienophiles. Success in these endeavors is anticipated to provide efficient access to a plethora of highly functionalized, biologically active polycyclic molecules, while also furthering fundamental understanding of structure and reactivity in this important area of reaction modality.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.