Catalytic Asymmetric Axially Chiral Allenyl C–P Bond Formation
Huanan Wang, Hui Qian, Junliang Zhang, Shengming Ma
Abstract
Chiral organophosphorous compounds are very important in catalysis, organic syntheses, and medicinal chemistry. However, catalytic enantioselective protocols for the axially chiral allenyl phosphorus compounds have never been reported. Herein, a palladium-catalyzed enantioselective carbon-phosphorus bond formation reaction affording axially chiral allenyl phosphonates has been developed. The reaction enjoys high yields and ees accommodating a wide range of functional groups. Mechanistic studies have unveiled an overwhelming kinetic resolution process.
Topics & Concepts
Enantioselective synthesisChemistryKinetic resolutionCatalysisAxial symmetryPalladiumAxial chiralityCombinatorial chemistryOrganic chemistryPhosphorusChirality (physics)Computational chemistryMedicinal chemistryChiral symmetry breakingSymmetry breakingEngineeringPhysicsQuantum mechanicsStructural engineeringNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis