CAREER: Versatility of Phosphorothioate Esters in the Synthesis of Sulfur-Containing Molecules

在这个由化学系化学合成项目和刺激竞争性研究实验项目办公室资助的项目中，达特茅斯学院的吉米·吴将探索合成含硫分子的新方法。 这将通过两种方法实现：1）醇、醚、甲硅烷基醚或苯甲酸酯的UV促进或镓催化的取代，和2）未活化烯烃的镓催化的氢硫醇化。 本申请的第二个目的是证明硫代磷酸酯在含硫分子的立体选择性合成中的用途。许多众所周知的生物活性药物如抗生素、抗炎剂和抗溃疡剂都含有硫。 含硫化合物在有机合成中也起着重要的作用，因为它们是广泛反应中有用的中间体。 考虑到硫在化学和生物学中的重要性，这是相当令人惊讶的是，相对较少的努力一直致力于这一研究领域。 该项目旨在开发制备这类重要化合物的新技术。 该提案的主要影响包括通过制作一系列关注有机化学中心主题的动画短片，提高普通人群对有机化学的认识和知识。 通过该项目的综合教育和研究活动，本科生和研究生将接受培训，并为学术界或工业界的职业生涯做好准备。

In this project, funded by the Chemical Synthesis program of the Division of Chemistry and the Office of Experimental Program to Stimulate Competitive Research, Jimmy Wu of Dartmouth College will explore novel methods for the synthesis of sulfur-containing molecules. This will be accomplished via two methods: 1) UV-promoted or gallium-catalyzed substitution of alcohols, ethers, silyl ethers, or benzoates, and 2) gallium-catalyzed hydrothiolation of unactivated alkenes. The second objective of this application is to demonstrate the utility of phosphorothioate esters in stereoselective syntheses of sulfur-containing molecules.Many well-known bioactive drugs such as antibiotics, anti-inflammatory agents, and anti-ulcerative agents, contain sulfur. Sulfur-containing compounds also play an important role in organic synthesis as they are useful intermediates in a wide range of reactions. Given the importance of sulfur in chemistry and biology, it is rather surprising that comparatively little effort has been devoted to this research area. This project seeks to develop new technologies for the preparation of this important class of compounds. A primary broader impact of this proposal includes increasing the awareness and knowledge of organic chemistry in the general population by creating a series of short, animated films which focus on central topics in organic chemistry. Through the integrated educational and research activities of this project, undergraduate and graduate students will receive training and be prepared for careers in either academia or industrial settings.