The enantioselective decarboxylative protonation (EDP) of malonic or acetoacetic acid derivatives is a synthetic methodology by which the chirality of the product is generated during the enol/enolate protonation step. Although EDP is a century-old reaction, it has not received much attention until recently. This review focuses on the EDP as an alternative to the strong-base-mediated deprotonation/asymmetric repro-
Thiourea derived cinchona alkaloids promote the asymmetric decarboxylative protonation of cyclic, acyclic, or bicyclic alpha-aminomalonate hemiesters under mild and metal-free conditions to afford enantioenriched aminoesters in high yields and enantioselectivities up to 93%. Both enantiomers of the aminoesters have been synthesized with the same selectivity when using organic base 3 and its pseudoenantiomer 6 derived from quinine.
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