5 years ago

About Underappreciated Yet Active Conformations of Thiourea Organocatalysts

About Underappreciated Yet Active Conformations of Thiourea Organocatalysts
Carsten Baldauf, Adriana Supady, Stefan Hecht
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 flexible molecules, especially when aiming for structure-based design of catalytic activity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01782

DOI: 10.1021/acs.orglett.7b01782

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