Kinetic Investigations of Product Inhibition in the Amino Alcohol-Catalyzed Asymmetric Alkylation of Benzaldehyde with Diethylzinc

Abstract

In situ reaction rate measurements help to define the role of product inhibition in the asymmetric alkylation of benzaldehyde with diethylzinc using (−)-MIB as a chiral reagent. Reaction calorimetry and kinetic modeling demonstrated that the rate behavior over consecutive reactions may only be rationalized when reversible binding of the product alkoxide is taken into consideration. These results may have implications for the conversion dependence of product enantioselctivity in reactions using enantioimpure catalysts.