Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis

Abstract

The metal free, single amino acid-catalyzed asymmetric desymmetrization (ADS) of meso-compounds 1 with nitrosobenzene 2 has been investigated using DFT. In this communication, we describe the role of electrostatic and dipole-dipole interactions in amino acid-catalyzed reactions, which has not previously been invoked in discussions of these important reactions. © The Royal Society of Chemistry 2006.