Water as a Direct Proton Source for Asymmetric Hydroarylation Catalyzed by a Rh(I)–Diene: Access to Nonproteinogenic β<sup>2</sup>/γ<sup>2</sup>/δ<sup>2</sup>-Amino Acid Derivatives
Jian‐Ping Chen, Yi Li, Chao Liu, Tianyi Wang, Lung Wa Chung, Ming‐Hua Xu
Abstract
A highly enantioselective rhodium-catalyzed intermolecular hydroarylation of α-aminoalkyl acrylates using water as a direct proton source has been realized by employing a chiral bicyclo[3.3.0] diene ligand, allowing efficient access to a broad range of α-aryl-methyl-substituted β2-, γ2-, and δ2-amino esters with excellent enantioselectivities (up to 98% ee) under exceptionally mild conditions. By utilizing this method, a series of structurally interesting benzo-fused heterocyclic molecules and the corresponding β2-, γ2-, and δ2-amino acids are facilely constructed.
Topics & Concepts
ChemistryCatalysisRhodiumDieneLigand (biochemistry)Intermolecular forceArylProtonEnantioselective synthesisMoleculeStereochemistryAmino acidMedicinal chemistryCombinatorial chemistryOrganic chemistryReceptorNatural rubberQuantum mechanicsAlkylBiochemistryPhysicsAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisSynthetic Organic Chemistry Methods