CAREER: Design and Synthetic Applications of New Multicomponent Reactions

职业：新型多组分反应的设计和合成应用

• 批准号: 0846189
• 负责人: Jared Shaw
• 金额: $ 58.14万
• 依托单位: University of California-Davis
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2009
• 资助国家: 美国
• 起止时间: 2009-08-01 至 2014-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0846189&HistoricalAwards=false
• 关键词: CAREER; Design; Synthetic; Applications; New

This award is funded under the American Recovery and Reinvestment Act of 2009 (Public Law 111-5).The Organic and Macromolecular Chemistry Program in the Chemistry Division at the National Science Foundation supports Professor Jared T. Shaw at the University of California at Davis. He will develop a new paradigm of reactivity that will enable the design and discovery of multicomponent reactions (MCRs). MCRs are reactions that form complex products from simple starting materials in a single operation, which can only emerge from a careful balance of reactivity that allows the successive bond-forming events to proceed in sequence. Among these reactions, the most valuable are those in which each of the components can be varied independently of the others. Professor Shaw has discovered a new four component reaction (4CR) that forms gamma-lactams in high yield with two or three stereogenic centers in high diastereoselectivity. Importantly, this "green" reaction takes place in a benign solvent and produces water as the only reaction by-product. This new 4CR forms the basis for a larger research program in this area that is described in the proposal. The studies that are proposed will demonstrate that the reactivity pattern observed has predictive value in the discovery of new reactions. The following outcomes of the proposed line of research are (1) new reactions of unprecedented efficiency for the assembly of heterocyclic compounds with multiple stereogenic centers, and (2) new approaches to the synthesis of complex natural products centered on MCRs for the assembly of core structures.MCRs and the synthesis of natural products targets will form conceptual nodes that can connect different areas of science as well as different sectors of society. Because MCRs offer the opportunity for rapid synthesis of molecules with interesting biological or physical properties, the PI will solicit collaborative projects from other departments that can be executed using this strategy. This approach will allow undergraduate students to learn how to make organic molecules and, more importantly, why their efforts are important to other disciplines. Professor Shaw will work with a high school class on the design and installation of an exhibit at the UC Davis arboretum that highlights the chemical components of medicinal plants native to California. The arboretum will provide an ideal setting for educating the public on the origin of chemical compounds used in medicines and inspire enthusiasm in further study of natural compounds through synthesis. The research and education plans described in the proposal will unite MCRs and chemical synthesis for the purpose of advancing the frontiers of science, educating the next generation of scientists, and connecting with the general public.

该奖项是根据2009年的《美国复苏与再现法案》（公法111-5）资助的。国家科学基金会化学部的有机和大分子化学计划支持加利福尼亚大学戴维斯分校的Jared T. Shaw教授。他将开发一个新的反应性范式，该范式将使多组分反应（MCR）的设计和发现。 MCR是在单个操作中从简单起始材料中形成复杂产物的反应，只能从仔细的反应性平衡中出现，从而使连续的键合事件可以按顺序进行。在这些反应中，最有价值的是每个组件都可以独立于其他组件变化的反应。 Shaw教授发现了一种新的四个成分反应（4CR），该反应以高产量形成γ-内酰胺，并以高映射性的两个或三个立体源性中心。重要的是，这种“绿色”反应发生在良性溶剂中，并产生水作为唯一的反应副产品。这个新的4CR构成了该领域中较大研究计划的基础，该计划在提案中描述了。提出的研究将证明观察到的反应性模式在发现新反应时具有预测价值。 The following outcomes of the proposed line of research are (1) new reactions of unprecedented efficiency for the assembly of heterocyclic compounds with multiple stereogenic centers, and (2) new approaches to the synthesis of complex natural products centered on MCRs for the assembly of core structures.MCRs and the synthesis of natural products targets will form conceptual nodes that can connect different areas of science as well as different sectors of 社会。由于MCR为具有有趣的生物学或物理特性的分子快速合成提供了机会，因此PI将征求可以使用此策略执行的其他部门的协作项目。这种方法将使本科生能够学习如何制作有机分子，更重要的是，为什么他们的努力对其他学科很重要。 Shaw教授将与高中班合作，在UC Davis Arboretum的设计和安装展览上，该展览突出了加利福尼亚州本地的药用植物的化学成分。植物园将为公众提供有关药物中化合物的起源的理想环境，并激发通过合成进一步研究天然化合物的热情。提案中描述的研究和教育计划将团结MCR和化学综合，以推进科学领域，教育下一代科学家，并与公众建立联系。