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基化反应的范围，以提供具有高对映选择性的仲烯丙醇。第二个目标是将得到的手性烯丙醇用于合成密集官能化的手性构筑块。使用单个反应容器，将探索导致多个C-C键和立体中心形成的串联反应。本课程将探讨将烯丙醇精制成各种有用的手性结构单元，包括烯丙基胺、烯丙基环丙烷和烯丙基环氧化物，并开发制备α-和β-氨基酸的方法。通过这一奖项，有机和高分子化学项目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。沃尔什博士将把他的工作重点放在开发方法上，以创建含有可用于指导反应性的官能团的手性构建块。具体地说，手性烯丙醇将成为目标。该项目可能会对有机合成产生重要的更广泛的影响，特别是在制药和农业行业。这项工作为本科生和研究生的培训提供了一个极好的场所，沃尔什教授与墨西哥科学家开展了出色的国际合作。

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.