Unraveling the Mechanism of the Cinchoninium Ion Asymmetric Phase-Transfer-Catalyzed Alkylation Reaction

The mechanism of the alkylation reaction of the indanone anion through asymmetric phase-transfer catalysis has been unraveled by density functional theory calculations. Our results point out that the present view of the asymmetry induction mechanism determined by hydrogen bond and pi-pi stacking interactions is not correct. Rather, stabilization of the main reaction pathway takes place through both the hydrogen bond and electrostatic interaction involving the leaving chloride anion.