Synthesis of Axially Chiral 2,2′-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution
Ziqing Zuo, Raphael S. Kim, Donald A. Watson
Abstract
-(iodo)arylphosphonates resulting in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This provides a practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands. The conditions have also proven effective for asymmetric dimerization of other, non-phosphorus-containing aryl halides.
Topics & Concepts
ChemistryHalideArylCombinatorial chemistryAxial symmetryCatalysisEnantioselective synthesisResolution (logic)Axial chiralityNickelCoupling (piping)Optically activeStereochemistryOrganic chemistryAlkylArtificial intelligenceStructural engineeringComputer scienceEngineeringMechanical engineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityChemical synthesis and alkaloids