Catalytic Asymmetric Benzylation of Azomethine Ylides Enabled by Synergistic Lewis Acid/Palladium Catalysis
Xin Chang, Jing-Di Ran, Xue‐Tao Liu, Chun‐Jiang Wang
Abstract
The synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a range of α-benzyl-substituted α-amino acid derivatives in satisfactory yield with excellent enantioselectivity. It is worth noting that this strategy exhibits good tolerance for bicyclic and monocyclic benzylic electrophiles. Furthermore, the utility of this synthetic protocol was demonstrated by the expedient preparation of enantioenriched antihypertensive drug α-methyl-l-dopa.
Topics & Concepts
ChemistryCatalysisLewis acids and basesPalladiumEnantioselective synthesisImineElectrophileYield (engineering)Chiral Lewis acidOrganic chemistryBicyclic moleculeCombinatorial chemistryMaterials scienceMetallurgyAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis