Cation-pi interactions are hypothesized to be one of many controlling factors in reaction selectivity, and we are interested in obtaining a better understanding of this supramolecular interaction as it relates to asymmetric catalysis.  Our group uses physical organic techniques, such as linear free energy relationships, to understand reaction mechanisms which includes the intermolecular interactions that aid in controlling these reactions.  In this talk we will show how we use our silylation-based kinetic resolution as a model reaction to explore how changes in the pi system of the substrate affect the selectivity of the reaction.  Since the hypothesized intermediate is a silylated cationic catalyst, changes in the substrate’s pi system should affect the affinity to the catalyst which ultimately affects the selectivity.  The effect of sterics and electronics will be presented as well as computational modeling to further understand this interaction. <br/>

Understanding the connection between cation-pi interactions and reaction selectivity

2019 Spring National Meeting

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