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Abstract:
Conformational dynamics can define the function of organocatalysts. While the accepted mechanism of Schreiner’s catalyst features a double hydrogen bond to the substrate that only forms with the anti-anti
conformation of its central thiourea
group, our electronic-structure theory study reveals that binding of the model substrate
methyl vinyl ketone prefers syn-anti
conformations. We find a new mechanism featuring Π stacking interactions and highlight the need for extensive structure searches for flexiblemolecules, especially when aiming for structure-based design of catalytic activity.
