Noncovalent interactions (NCIs) are the collection of both favorable and unfavorable interactions between molecules, such as hydrogen-bonding, ion-dipole, and π-π interactions. These interactions are at the core of asymmetric catalysis using chiral catalysts to convert an achiral or prochiral substrate to a chiral product. Squaramide organocatalysts (SQs) are a privileged type of catalyst that can catalyze a wide variety of reactions by taking advantage of NCIs via one of two main modes of activation – either dual activation or chiral anion catalysis. The latter type involves a chiral ion pair and has been of interest recently based on the discovery of a chiral, SN1-type alkylation developed by Jacobsen. We are interested in extending this system to other allylic and propargylic substrates and a variety of nucleophiles. This presentation will describe the results of our work utilizing synthesized achiral squaramide organocatalysts to more quickly and cost effectively screen reactions. The products are small, chiral building blocks that provide a valuable derivatization of petroleum feedstocks.

Exploration of an organocatalyzed asymmetric nucleophilic addition to allylic and propargylic substrates

ACS Spring 2022

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