Chiral surface control in the Soai reaction: a DFT study of α-quartz-induced enantioselective autocatalysis

Abstract

The mechanism of enantioselectivity generation in the Soai reaction induced by chiral α-quartz surfaces was modeled using DFT computations. Analyzing transition states for S- and R-product formation on d- and l-quartz revealed key stabilizing interactions, including hydrogen bonding and zinc coordination with the surface. Computed mirror-symmetric energy profiles for the reactions with d- and l-quartz systems correspond to the experimentally observed handedness of the product and demonstrate how the surface chirality controls the stereochemistry of the reaction.