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，寻求开发以最大化可持续发展的方式组装复杂有机分子的新策略。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。该项目将能够合成有机分子，最终可能成为具有有用特性的新药或其他材料，同时将与许多当前技术相关的对环境的负面影响降至最低。该项目的中心是利用酸酐作为亲核剂的潜力，并能够以很少的副产品合成复杂的有机分子。这些转化有助于在温和的条件下进行，无论是在没有额外试剂的情况下，还是在有机催化剂的帮助下发生，有机催化剂是过渡金属催化剂的一种良性替代品。这些新的转变产生新的有机结构的能力将在从植物钩吻属物种衍生的天然产品的构建中得到展示。天然产品为这个项目的研究和推广提供了一个压倒一切的主题。除了是这项研究的最终目标外，从植物中提取的化学物质作为药物的特性的演示使这项研究能够在许多层面上与普通公众建立联系。以自然产品为中心的推广活动包括一年一度的科学咖啡馆，以吸引普通公众，为当地高中生到加州大学戴维斯分校植物园进行实地考察，以及参加一年一度的盲人和视障(BVI)初中生和高中生化学夏令营。

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.