Publication

In depth analysis of heterogeneous catalysts for the chemoenzymatic dynamic kinetic resolution of beta-amino esters

Kumar Varoon Agrawal, Cédric Karel J Van Goethem
2022
Journal paper

Abstract

The chemoenzymatic dynamic kinetic resolution of beta-amino esters is established after detailed evaluation of metal-based heterogeneous catalysts for racemization and enzyme catalysts for kinetic resolution. Several heterogeneous palladium catalysts proved to be able to perform racemization of the model substrate, propyl beta-phenylalaninate. The catalysts were characterized and their kinetics evaluated to eventually select two different but promising racemization catalysts. Relations were established between physical catalyst characteristics and the selectivities in the racemization and DKR reactions. By combining racemization with the kinetic resolution, an efficient DKR was realized with excellent enantioselectivity and yields for a significant scope of beta-amino esters.

Official source

https://infoscience.epfl.ch/record/292720?ln=en

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Related concepts (30)

Kinetic resolution

In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials.

Catalysis

Catalysis (kəˈtæləsɪs) is the process of change in rate of a chemical reaction by adding a substance known as a catalyst (ˈkætəlɪst). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

Asymmetric hydrogenation

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer.

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