Synthesis of Chiral Building Blocks

本研究的第一个目标是优化和扩大醛的不对称乙烯化反应，以获得高对映选择性的仲烯丙醇。 第二个目标是使用所得的手性烯丙醇在合成致密官能化的手性结构单元。 使用一个单一的反应容器，串联反应导致多个C-C键和立体中心的形成将进行探索。 将研究烯丙基醇与各种有用的手性结构单元的酯化反应，包括烯丙基胺、烯丙基环丙烷和烯丙基环氧化物，研究将开发制备α-和β-氨基酸的方法。有了这个奖项，有机和高分子化学计划正在支持宾夕法尼亚大学化学系的帕特里克J.沃尔什博士的研究。 沃尔什博士的工作重点将是开发用于创建手性结构单元的方法，这些结构单元含有可用于指导反应性的官能团。 具体而言，手性烯丙醇将成为目标。该项目可能对有机合成产生重要的广泛影响，特别是在制药和农业工业中。 这项工作为本科生和研究生的培训提供了一个很好的场所，沃尔什教授与墨西哥科学家建立了良好的国际合作。

The first objective of this research is to optimize and expand the scope of the asymmetric vinylation of aldehydes to furnish secondary allylic alcohols with high enantioselectivity. The second objective is to use the resulting chiral allylic alcohols in the synthesis of densely functionalized chiral building blocks. Using a single reaction vessel, tandem reactions resulting in the formation of multiple C-C bonds and stereocenters will be explored. Elaboration of the allylic alcohols to a variety of useful chiral building blocks including allylic amines, allylic cyclopropanes and allylic epoxides will be examined and the research will develop methods for the preparation of alpha- and beta- amino acids. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Patrick J. Walsh of the Department of Chemistry at the University of Pennsylvania. Dr. Walsh will focus his work on the development of methodologies for the creation of chiral building blocks containing functional groups useful for directing reactivity. Specifically, chiral allylic alcohols will be targeted. The project could have important broader impact on organic synthesis, in particular in the pharmaceutical and agricultural industries. The work provides an excellent venue for the training of both undergraduate and graduate students and Professor Walsh has developed excellent international collaborations with Mexican scientists.