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 π–π 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.