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

职业：复杂环系收敛合成的新周环方法

• 批准号: 2340210
• 负责人: Christopher Newton
• 金额: $ 77万
• 依托单位: University of Georgia Research Foundation Inc
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2024
• 资助国家: 美国
• 起止时间: 2024-03-01 至 2029-02-28
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2340210&HistoricalAwards=false
• 关键词: CAREER; New; Pericyclic; Methodologies; Convergent

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.

在化学系化学合成项目的支持下，乔治亚大学的克里斯托弗·牛顿正在设计新型分子“构件”，以提高分子加成反应的反应性和多功能性。这些加成反应能够快速构建复杂的有机物。通过连接两个更简单的片段来形成分子，这项研究旨在解决该领域长期存在的限制其应用的挑战，预计目标反应将产生包含碳、氧和氮原子的多种环状结构。机制的详细研究这项研究的成果将产生广泛的科学和社会影响，包括在制药、材料和农用化学品行业。牛顿博士和他的团队将致力于培养本科生和研究生掌握最先进的化学技术，帮助加强美国未来的 STEM（科学、技术、工程和数学）劳动力队伍。并传播免费、开放获取的化学最后，该奖项将与当地高中教师合作，支持一项外展计划，为佐治亚州雅典大社区提供实践实验室经验和职业指导。在克里斯托弗·牛顿（Christopher Newton）的指导下，该研究计划的重点是开发新的、基于周环的策略，用于高价值复杂环系统的聚合合成。这项研究旨在调整环加成反应的反应性，包括古老的狄尔斯-阿尔德反应，通过与当前最先进的方法相比，使用非典型的高氧化态结构单元连接这些新颖的片段可以提高产品的复杂性和功能性。该研究计划具有三个不同的目标：（i）开发。交叉偶联活性狄尔斯-阿尔德二烯的第一个一般家族，（ii）一步狄尔斯-阿尔德/环扩展路线至7元和8元杂环和碳环基序，以及（iii）开发新型、高反应性的氮杂亲双烯体预计将提供对大量高度功能化、生物活性的多环分子的有效获取，同时也进一步加深对这一重要反应方式领域的结构和反应性的基本理解。该奖项符合 NSF 的法定使命，并通过评估被认为值得支持，反映了使用基金会的智力优点和更广泛的影响审查标准。