title: Asymmetric synthesis of QUINAP via dynamic kinetic resolution.
abstract: A palladium-catalyzed, atroposelective C-P coupling process has been developed for the asymmetric synthesis of QUINAP and its derivatives in high enantiomeric excess. Bromide, triflate (OTf) and 4-methanesulfonylbenzenesulfonate (OSs) precursors were studied, leading in the case of the triflate to a novel dynamic kinetic resolution involving isomerization of an arylpalladium intermediate. The operationally simple methods described in this communication afford these important ligands in good to high yields and selectivity using low catalyst loading (≤3 mol % Pd).
authors.affiliation: Caltech Center for Catalysis and Chemical Synthesis, Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California, 91125, United States.
authors.forename: Vikram
authors.initials: V
authors.lastname: Bhat
authors.forename: Su
authors.initials: S
authors.lastname: Wang
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
authors.forename: Scott C
authors.initials: SC
authors.lastname: Virgil