Computational Insights into Cinchona‐Based Phase Transfer Catalysisfor Asymmetric Conjugate Cyanation

• Published in: European journal of organic chemistry
• Main Authors: Iribarren, Iñigo, Ferrer, Maxime, Alkorta, Ibon, Trujillo, Cristina
• Format: Journal Article
• Language: English
• Published: 17-05-2024
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202400329

The synthesis of asymmetric organic molecules has experienced a huge development over the last
few decades. Phase‐transfer catalysis has been proven to be one of the most powerful methods
for these asymmetric transformations. However, the study of the mechanism of these catalysts and
the different interactions that they can establish with the reactants has failed to keep pace. In the
present study, the conjugate cyanation of two different α,β‐unsaturated ketones are studied in the
presence of a well‐known alkaloid quinine‐derived PTC, along with different modifications. The study
includes the comparison of different binding modes between the catalysts and the different reactants,
the mechanistic study of the reaction and the analysis of the non‐covalent interactions established
within the complexes and their role in the global enantioselectivity of the process.