Development of Diiron Bridging Acyl Complexes in Organic Synthesis

这项研究的重点是开发改进的方法来合成光学纯有机化合物，使用含有手性硫醇的α，β-不饱和酰基二铁羰基络合物。这些试剂与硝酮反应生成不对称的异恶唑烷。将进行结构研究，以确定观察到的产品选择性的来源，并将异恶唑烷用作合成光学活性β-氨基酸和β-内酰胺的中间体。酰基二铁络合物还将用于不对称Diels-Alder反应中的丁腈氧化物的区域选择性加成，以及用作不对称Michael加成的有机金属组分。通过这一续展奖项，有机和高分子化学项目为华盛顿大学化学系的Scott R.Gilbertson博士的研究提供了持续的支持。吉尔伯森教授的研究重点是开发新的和改进的合成方法来制备有机化合物。该方法以有机金属试剂为基础，有可能用于制备具有有趣生物学特性的有机化合物。在这项工作中，学生将接受有用的培训，以发展制药行业非常感兴趣的合成技能。

The focus of this research is the development of improved methods for the synthesis of optically pure organic compounds, using alpha,beta-unsaturated acyl diiron carbonyl complexes incorporating a chiral thiol. Reactions of these reagents with nitrones results in the formation of asymmetric isoxazolidines. Structural studies will be carried out to determine the origin of the observed product selectivities, and the isoxazolidines will be used as intermediates in the synthesis of optically active beta-amino acids and beta-lactams. The acyl diiron complexes will also be used in asymmetric Diels-Alder reactions in the regioselective addition of nitrile oxides, and as organometallic components for the asymmetric Michael addition. With this renewal award, the Organic and Macromolecular Chemistry Program provides continuing support for the research of Dr. Scott R. Gilbertson of the Department of Chemistry at Washington University. Professor Gilbertson's research is focused on developing new and improved synthetic methods for the preparation of organic compounds. The methodology, based on organometallic reagents, has potential for use in the preparation of organic compounds having interesting biological properties. In this work, students will receive training useful in developing synthetic skills of great interest to the pharmaceutical industry.