A MECHANISTIC APPROACH TO ASYMMETRIC KETONE ARYLATION

Massachusetts Institute Of Technology, Cambridge MA

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Abstract

A synthetic and mechanistic approach is proposed to facilitate understanding and improvement of the palladium-catalyzed asymmetric alpha-arylation of ketones. Limitations to the current methodology will be explored in the context of three main aspects of the reaction: ligand coordination, base reactivity, and substrate specificity. Screening of a variety of ligands and different bases will set the foundation for advancement of the current methods. Kinetic studies will reveal insights into the mechanism of the arylation reaction and undesirable side reactions. The information learned will lead to methodology that can improve the overall yield, enantioselectivity and generality of the arylation of ketones. The synthesis of chiral alpha-aryl ketones is important for the formation of enantiomerically-pure, pharmaceutically- relevant compounds and their precursors.