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

Abstract

Mechanism of enantioselectivity generation in theSoai reaction induced by chiral α-quartz surfaces was modeled by DFT computations. Analyzing transition states for S-and R-products 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 stereochemistry of the reaction.