ENANTIOSELECTIVE SYNTHESIS OF PLANAR-CHIRAL PHOSPHINES WITH 1,N-DIOXANPARACYCLOPHANE SCAFFOLD AND THEIR APPLICATION AS CHIRALLIGANDS

摘要

A new family of chiral phosphines based on planar-chiral 1 ,n-dioxanparacyclophane scaffold was created. They were synthesized with excellent enantioselectivity via asymmetric ortho-lithiation using sec-butyllithium and (-)-sparteine. These phosphines were used as chiral ligands in three reactions: Ag-catalyzed allylation of imines, Pd-catalyzed asymmetric Sonogashira coupling of diiodoparacyclophanes, and Pd-catalyzed asymmetric Suzuki-Miyaura coupling of tricarbonyl(η~6-ortho-dichlorobenzene)chromium.