Any reaction that results in the loss of one or more symmetry elements, but especially the conversion of a prochiral molecule into a chiral one is called desymmetrization. Desymmetrization has become one of the most important, elegant and powerful strategies in asymmetric synthesis in the last 20 years. Enantioenriched molecules can be prepared from achiral or meso starting molecules by using organocatalysts such as Cinchona alkaloids.

Enantioselective Desymmetrization

The asymmetric introduction of new stereocenters is considered one of the most stimulating challenges in organic chemistry, and has a great impact on related fields such as medicine and biology. Enantioselective desymmetrization represents a powerful strategic framework and enables the conversion of relatively simple achiral starting materials to high-value stereochemically rich products. A range of available feedstocks, including cyclic anhydrides, ketones, diketones, diols, enones, dienes, small rings, and other prochiral substrates, can be used in organocatalytic desymmetrizing processes in a stereocontrollable fashion.

Especially Cinchona alkaloid compounds, used as chiral organocatalysts, have attracted considerable attention since it produces chiral compounds in high yields and with remarkable high enantioselectivity.

Please enter the free of charge Chiral Catalyst Search Data Base to review lots of enantioselective desymmetrization examples.

Example from literature

Preparation method for Brivaracetam and intermediate therof. (Guo, P., Liu, F., Ren, J., Zhu, W.; WO2020051796A1, 2020)