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.