Designing Catalysts for Asymmetric C-C Bond Formations

Stanford University, Stanford CA

Investigators

Linked publications & trials

Abstract

DESCRIPTION (provided by applicant): Biological functions are controlled in large part by molecular recognition. Biological receptors recognize and bind specific chiral molecules that act as messengers in the human body. By studying the responses that different molecules elicit from a receptor, researchers can learn more about the structure of the receptor and the biological process that it controls. The cures of many illnesses rely on the understanding and the regulating of these biological functions. Therefore, development of an efficient synthetic tool to construct chiral molecules is important to the study of these systems and the discovery of new chemotherapeutic agents that would prohibit or inhibit such processes. Palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) reactions offer a more efficient, cost-effective method to synthesize highly desired chiral molecules. Currently, the catalyst systems broadest in scope employ palladium complexes of Trost ligands. We propose to increase the scope of this process by developing a better understanding of how the Trost ligand binds to the palladium through stepwise ligand modification. The results of our study should tell us more about what influences catalyst selectivity. In addition, we will synthesize hybrid ligands based on the combination of the beneficial properties of Trost and P,N-ligands, and apply their palladium complexes to underdeveloped asymmetric reactions of allylic electrophiles with organozinc and -magnesium nucleophiles. Overall, we intend to increase the scope of Pd-AAA reactions, which is a powerful tool for the synthesis of biologically important chiral molecules.