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Improving Phase-Transfer Catalysis by Enhancing Non-Covalent Interactions

preprint
submitted on 18.04.2020 and posted on 23.04.2020 by Iñigo Iribarren, Cristina Trujillo

A wide variety of asymmetric transformations catalysed by chiral catalysts have been developed for the synthesis of valuable organic compounds in the past several decades. Within asymmetric catalysis field, phase-transfer catalysis has been recognized as a powerful method for establishing useful procedures for organic synthesis. In the present study intermolecular interactions between a well-known alkaloid quinine-derived phase transfer catalyst and four different anions were characterised, analysing the competition between the pure ion-pair interaction and the intermolecular hydrogen bond established upon complexation. Finally, the energy profile corresponding to the enantioselective conjugate cyanation of a a,b-unsaturated ketone, under the presence of two different catalysts were performed.

Funding

SFI 18/SIRG/5517

History

Email Address of Submitting Author

trujillc@tcd.ie

Institution

Trinity College Dublin

Country

Ireland

ORCID For Submitting Author

0000-0001-9178-5146

Declaration of Conflict of Interest

No conflict of interest

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in Physical Chemistry Chemical Physics

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