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About Underappreciated Yet Active Conformations of Thiourea Organocatalysts

MPG-Autoren
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Supady,  Adriana
Theory, Fritz Haber Institute, Max Planck Society;

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Baldauf,  Carsten
Theory, Fritz Haber Institute, Max Planck Society;

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acs.orglett.7b01782.pdf
(Verlagsversion), 2MB

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Zitation

Supady, A., Hecht, S., & Baldauf, C. (2017). About Underappreciated Yet Active Conformations of Thiourea Organocatalysts. Organic Letters, 19(16), 4199-4202. doi:10.1021/acs.orglett.7b01782.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-002D-CB9B-8
Zusammenfassung
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.