New Stereoselective Fragment Coupling Reactions for Organic Synthesis

有了这个新的奖项，化学合成计划支持西北大学的Regan J. Thomson教授研究新的反应，使两个或多个分子片段的偶联产生具有特定分子形状的新分子。 这些反应在药物发现领域将特别强大，并最终促进新的生物活性实体可以制备用于进一步评估的速率。这些研究将使学生接触到各种研究领域，包括合成设计，催化，方法学开发以及使用质谱技术筛选产品。参与本项目的本科生和研究生将参与指导芝加哥地区高中生的研究项目。本项目将研究利用N-烯丙基腙和N-磺酰腙形成新的碳-碳键的反应。该方法将涉及烯丙基腙氧化为重氮联烯，然后进行立体选择性[3，3]-重排，形成新的碳-碳键，最终产生碳阳离子，可以用外部亲核试剂捕获。此外，磺酰腙将用于新的碳-碳键形成反应。这些立体选择性的片段偶联反应将被用于合成具有生物活性的天然产物。

With this New award, the Chemical Synthesis Program supports Professor Regan J. Thomson of Northwestern University in an investigation of new reactions that enable the coupling of two or more molecular fragments to generate new molecules with specific molecular shapes. These reactions will be especially powerful within the realm of drug discovery, and ultimately facilitate the rate at which new biologically active entities can be prepared for further evaluation. These studies will expose students to a diversity of research areas including synthesis design, catalysis, methodology development, and the use of mass spectrometric techniques to screen products. The undergraduates and graduate students participating in this project will be involved in mentoring the research projects of Chicago area high school students.The project will study new carbon-carbon bond forming reactions utilizing N-allylhydrazones and N-sulfonylhydrazones. The approach will involve the oxidation of allyl hydrazones to diazoallenes, which then undergo a stereoselective [3,3]-rearrangement with the formation of a new carbon-carbon bond ultimately producing carbocations, which can be trapped with external nucelophiles. In addition, sulfonyl hydrazones will be utilized in new carbon-carbon bond forming reactions. These stereoselective fragment coupling reactions will be employed in the systhesis of biologically active natural products.