Palladium(II)-Catalyzed Enantioselective Hydrooxygenation of Unactivated Terminal Alkenes
Xintuo Yang, Xiang Li, Pinhong Chen, Guosheng Liu
Abstract
A novel Pd(II)-catalyzed enantioselective Markovnikov hydrooxygenation of unactivated terminal alkenes using a substituted pyridinyl oxazoline (Pyox) ligand has been developed. Herein it was discovered that the (EtO)2MeSiH/BQ redox system is vital for the highly selective and efficient hydrooxygenation, where the alkylpalladium(II) species generated from enantioselective oxypalladation step is reduced by silane. This method provides efficient access to optically pure alcohol esters from easily available alkenes with excellent enantioselectivities and features a broad substrate scope.
Topics & Concepts
Enantioselective synthesisChemistryMarkovnikov's ruleCatalysisOxazolineSubstrate (aquarium)Combinatorial chemistryLigand (biochemistry)PalladiumOrganic chemistryRegioselectivityReceptorBiochemistryGeologyOceanographyAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions