Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 995-1001Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02486
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Funding
- Poland's National Science Centre [2016/21/B/ST5/03352]
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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.
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.
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