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Issue 37, 2020
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Improving phase-transfer catalysis by enhancing non-covalent interactions

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Abstract

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 the 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, a theoretical study of the free-energy profile corresponding to the enantioselective conjugate cyanation of an α,β-unsaturated ketone in the presence of two different catalysts was performed.

Graphical abstract: Improving phase-transfer catalysis by enhancing non-covalent interactions

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Article information


Submitted
14 Apr 2020
Accepted
08 Jul 2020
First published
08 Jul 2020

Phys. Chem. Chem. Phys., 2020,22, 21015-21021
Article type
Paper

Improving phase-transfer catalysis by enhancing non-covalent interactions

I. Iribarren and C. Trujillo, Phys. Chem. Chem. Phys., 2020, 22, 21015
DOI: 10.1039/D0CP02012E

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