Achiral Reaction Systems in the Simulation of the Kinetic Resolution of Acid Reagents via Reactions with Epoxides under Zero Order in Enantiomers

Abstract

Kinetic resolution is one of the general methods for the separation of racemic mixtures into individual enantiomers. Most kinetic resolution reactions are characterized by the first order in enantiomers. In this work we were the first to perform experimental simulation of the kinetic resolution of acidic proton-donor nucleophilic reagents under zero-order conditions with respect to the proton donor via their reaction with oxiranes. Appropriate model achiral reaction systems were proposed, and the corresponding kinetic parameters, including reaction orders in the reactants and observed and catalytic rate constants were determined. The results showed that kinetic resolution of racemates under zero-order conditions provides efficient separation into individual enantiomers even in the case of small difference in enantioselectivity.