An efficient method has been developed for the rapid computational analysis and redesign of existing stereoselective catalysts. Graphical Processing Unit (GPU) accelerated quantum mechanics and in-house conformational clustering protocols allow for the rapid computation of geometries and energies for all chemically relevant structures. Finally, high-accuracy quantum mechanical energy refinements are used to reproduce experimental selectivities.  These strategies and tools were applied towards the redesign of two organocatalytic reactions:  1) a bifunctional thiourea-catalyzed Michael reaction and 2) an N-heterocyclic carbene-catalyzed �-addition to a-ketophosphonates. Factors that control the selectivity in both these examples, the subsequent redesigned catalysts, and limitations are discussed.

Strategies and tools towards efficient computational rationalization and redesign of catalysts for synthetic organic chemistry

245th National Meeting (2013)

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