Due to the difficulty of enantiomeric separations and the common desire to increase synthetic yield, gaining enantioselective control through the asymmetric catalysis of reactions is an important goal. Unfortunately, finding the right catalyst to drive a reaction towards a single enantiomeric product is difficult. Non-covalent organocatalysts are a popular choice for such asymmetric reactions. Experimental evidence shows some cinchonidine-derived catalysts can drive partial asymmetry in the [2,3]-Wittig rearrangement of 3-(allyloxy)-1-benzyl-2-oxindole while maintaining high synthetic yields. If we can properly model these reactions computationally, we will be able to design new, more effective catalysts. In order to better predict the enantioselectivity of these non-covalent organocatalysts, we have implemented agglomerative clustering algorithms to sample molecular dynamics trajectories.  This approach ensures a complete picture of the conformational potential energy surface is considered.  The key structures identified are then studied using multi-stage geometry optimization and frequency analysis. Through this method we aim to more accurately determine the global minima and transition states on that potential energy surface which will lead to more accurate enantioselectivity calculations.<br/>

Agglomerative clustering for potential energy surface sampling of the non-covalent organocatalyzed, asymmetric [2,3]-Wittig rearrangement

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.