Catalytic Enantioselective Benzilic Ester Rearrangement
Hua Wu, Qian Wang, Jieping Zhu
Abstract
Abstract We report the first examples of catalytic enantioselective benzilic ester rearrangement reaction. In the presence of a catalytic amount of Cu(OTf) 2 and a chiral box ligand under mild conditions, reaction of 2,3‐diketoesters with alcohols afforded structurally diverse α‐aryl(alkyl) substituted‐α‐hydroxy malonates (tartronic esters) in good to excellent yields with high enantioselectivities. Preliminary mechanistic studies indicated that hemiketalization, rather than the dynamic kinetic resolution of hemiketal, was the enantiodetermining step under our reaction conditions.
Topics & Concepts
Enantioselective synthesisChemistryCatalysisLigand (biochemistry)Kinetic resolutionArylAlkylCatalytic cycleOrganic chemistryMedicinal chemistryReceptorBiochemistryAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisSynthetic Organic Chemistry Methods