SusChEM: Beyond Acylation: New Methodology and Mechanistic Studies of Anhydrides for Stereoselective Synthesis

通过这个项目，加州大学戴维斯分校的Jared Shaw教授在可持续化学，工程和材料（SusChEM）倡议（化学合成计划，化学部）的资助下，寻求开发新的策略，以最大限度地提高可持续性的方式组装复杂的有机分子。实验室实验将利用计算化学的预测能力来设计和开发新的反应。该项目将使有机分子的合成最终成为新的药物或其他具有有用特性的材料，同时最大限度地减少与许多现有技术相关的对环境的负面影响。该项目的重点是利用酸酐作为亲核试剂的潜力，并使合成复杂的有机分子的副产物很少。这些转化通过在温和条件下在不存在额外试剂的情况下或在有机催化剂的帮助下发生而有助于可持续性，有机催化剂作为过渡金属基催化剂的良性替代品。这些新的转化产生新的有机结构的能力将在来自Gelsimium植物物种的天然产物的构建中得到证明。天然产品为该项目的研究和推广提供了一个压倒一切的主题。除了作为研究的最终目标之外，植物化学品作为药物的特性的演示使这项研究能够在许多层面上与公众联系起来。以天然产品为中心的外展活动包括一年一度的科学咖啡馆，以吸引公众，实地考察当地高中学生到加州大学戴维斯分校植物园，并参加一年一度的盲人和视力障碍（BVI）初中和高中学生化学营。

With this project, Prof. Jared Shaw of the University of California, Davis, funded under the Sustainable Chemistry, Engineering, and Materials (SusChEM) initiative (Chemical Synthesis Program, Chemistry Division), seeks to develop new strategies for assembling complex organic molecules in ways that maximize sustainability. Laboratory experiments will take advantage of the predictive power of computational chemistry in the design and development of new reactions. This project will enable the synthesis of organic molecules that might eventually become new medicines or other materials with useful properties while minimizing the negative impacts on the environment associated with many current techniques. This project is centered on harnessing the potential of anhydrides to act as nucleophiles and to enable the synthesis of complex organic molecules with few byproducts. These transformations contribute to sustainability by occurring under mild conditions either in the absence of additional reagents or with the assistance of an organocatalyst, which serves as a benign alternative to transition metal-based catalysts. The ability of these new transformations to produce new organic architectures will be demonstrated in the construction of natural products derived from the Gelsimium species of plant. Natural products provide an over-riding theme for both research and outreach in this project. In addition to being an end-goal of the research, demonstrations of the properties of chemicals from plants as medicines enables this research to connect with the general public on many levels. Natural product-centered outreach includes an annual Science Café to engage the general public, field trips for local high school students to the UC Davis Arboretum, and participation in an annual Chemistry Camp for Blind and Visually Impaired (BVI) junior high and high school students.