Stereoselective Indium-Mediated Reactions for Organic Synthesis

用于有机合成的立体选择性铟介导反应

• 批准号: 0616485
• 负责人: Gregory Cook
• 金额: $ 52.7万
• 依托单位: North Dakota State University Fargo
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2006
• 资助国家: 美国
• 起止时间: 2006-10-01 至 2010-12-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0616485&HistoricalAwards=false
• 关键词: Stereoselective; Indium; Mediated; Reactions; Organic

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.

该项目通过三组互补的研究来解决铟介导的反应化学的发现和发展。将评估烯丙基卤化物的铟（+3）活化的广度和范围，包括分子内和分子间的frieel - crafts芳基化，以及检查其他亲核试剂。非映对和对映选择性铟介导的腙烯丙基化也将被探讨。最后，将研究铟介导的醛和亚胺烯丙化反应，利用钯催化生成反应性铟配合物。手性胺和醇存在于各种各样的生物活性分子中，选择性和环境友好的制备方法的发现和发展是一个持续的挑战。通过这个奖项，有机和大分子化学项目支持了位于法戈的北达科他州立大学化学系的Gregory R. Cook博士的研究。库克教授制定了新的铟介导的方法来合成手性胺和醇，并利用这些方法合成生物活性化合物。金属铟作为有机反应的促进剂，由于其相对较低的毒性和与环境友好的溶剂的相容性而具有重要意义。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新不对称生态友好工艺奠定了基础。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。