Enantioselective Synthesis of <i>P</i>-Chiral Phosphine Oxides Bearing an All-Carbon Quaternary Stereogenic Center via Palladium-Catalyzed Domino Heck–Suzuki Reaction
Siyu Zhao, Jiahao Liu, Xunfang Xu, Xue‐Mei Chen, Terumasa Kato, Zhe Wang, Yan Liu, Keiji Maruoka
Abstract
An approach has been developed for the enantioselective synthesis of P -chiral phosphine oxides bearing an all-carbon quaternary stereogenic center via a Pd-catalyzed domino Heck–Suzuki reaction. The origin of the mechanistic preference leading to high diastereo- and enantioselectivities under the Pd catalysis based on a TADDOL-derived phosphoramidite ligand was rationalized on the basis of DFT calculations.
Topics & Concepts
StereocenterEnantioselective synthesisPalladiumDominoCatalysisChemistryPhosphineQuaternary carbonHeck reactionOrganic chemistryCombinatorial chemistryStereochemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods