Synthesis of Chiral Building Blocks

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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.