Asymmetric Reductive Cyclization of Tethered Aryl Halides in Pursuit of TunePhos-Type Ligands

Researcher(s)

  • Jacob Letnaunchyn, Chemistry, University of Delaware

Faculty Mentor(s)

  • Don Watson, Department of Chemistry and Biochemistry, University of Delaware

Abstract

Bridged axially chiral biaryl scaffolds are a naturally occurring structure in nature.  Axial chirality occurs around the aryl-aryl C-C bond due to a nonplanar arrangement of tetra ortho-substituted biaryl structures. These structures are also excellent at chirality transfer making them efficient ligands for catalysis.  TunePhos ligands are a class of biaryl compounds which have a conformationally rigid yet tunable chiral axis. This rigidity results from a tether by which changing the length, can tune the dihedral angle of the biaryl axis. Utilizing previous advancements from our group in intermolecular asymmetric reductive cross-couplings and tethered aryl halides will allow for a streamlined and efficient synthesis of TunePhos type ligands.