Stereoselective Indium-Mediated Reactions for Organic Synthesis

该项目通过三组相辅相成的研究来解决铟介导的反应化学的发现和发展。将对烯丙基卤化物的铟(+3)活化的广度和范围进行评估，包括分子内和分子间的Friedel-Craft芳基化反应，以及检查其他亲核试剂。我们还将探讨铟的非对映选择性和对映体选择性催化的酰肼的烯丙基化反应。最后，将研究铟催化的醛和亚胺的烯丙化反应，利用钯催化生成活性铟配合物。手性胺和醇存在于各种生物活性分子中，发现和开发选择性和环境友好的方法制备它们是一个持续的挑战。通过这一奖项，有机和高分子化学项目支持了北达科他州立大学法戈分校化学系的格雷戈里·R·库克博士的研究。库克教授提出了以铟为媒介的新方法来合成手性胺和醇，并利用这些方法合成了具有生物活性的化合物。金属铟作为有机反应的促进剂具有非常重要的意义，因为它的毒性相对较低，而且与环境友好的溶剂相容。库克教授在铟介导的温和环化化学方面的研究为有机合成的不对称生态友好型新工艺奠定了基础。来自塞拉利昂、中国、印度、日本和美国的学生参加了这个研究项目。

This project addresses the discovery and development of indium-mediated reaction chemistry through three complementary sets of studies. The breadth and scope of indium(+3) activation of allyl halides will be evaluated, encompassing intra- and intermolecular Friedel-Crafts arylations and examining other nucleophiles as well. Diastereo- and enantioselective indium-mediated allylation of hydrazones will also be explored. Finally, indium-mediated allylation of aldehydes and imines will be studied, utilizing palladium catalysis to generate the reactive indium complexes.Chiral amines and alcohols are found in a wide variety of biologically active molecules, and the discovery and development of selective and environmentally benign methods for their preparation represents an ongoing challenge. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Gregory R. Cook, of the Department of Chemistry at North Dakota State University at Fargo. Professor Cook has formulated new indium-mediated methods for the synthesis of chiral amines and alcohols and has utilized these methods for the synthesis of biologically active compounds. The utility of indium metal as a promoter of organic reactions is highly significant due to its relatively low toxicity and compatibility with environmentally benign solvents. Professor Cook's studies in indium-mediated mild cyclization chemistry set the stage for new asymmetric eco-friendly processes for organic synthesis. Students from Sierra Leone, China, India, Japan and the US are participating in this research program.