Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts

We report an enantioselective phase transfer alpha-chlorination of beta-keto esters catalyzed by hybrid amide-based Cinchona derivatives. The chlorination process proceeds with proper quantitative yields (up to <99%) and high asymmetric induction (up to 97% ee). We show that the use of only 0.5 mol % hybrid catalyst based on a Cinchona core allows the chlorination reaction to be conducted in a highly enantioselective manner with various indanone and tetralone carboxylate esters.

Automated summary

In this study, an enantioselective phase transfer alpha-chlorination of beta-keto esters catalyzed by hybrid amide-based Cinchona derivatives was successfully reported. The reaction showed proper quantitative yields and high asymmetric induction, with use of only 0.5 mol % hybrid catalyst based on a Cinchona core allowing for highly enantioselective chlorination with various substrates.