Facile Synthesis of Structurally Diverse 3,3′-Disubstituted 1,1′-Binaphthyl-2,2′-diamines in Optically Pure Forms

  • 10.1021/jo8011368
  • The Journal of Organic Chemistry
  • p 7387-7389, Volume 73, Issue 18,
  • journal-article
A new synthetic route to 3,3′-dihalo BINAMs based on the direct halogenation of H 8 -BINAM and subsequent rearomatization to the binaphthyl core has been developed. The combination of this new procedure and Pd-catalyzed coupling reactions enabled us to synthesize various 3,3′-disubstituted BINAMs in only three steps starting from H 8 -BINAM.


Simple BINAM ligand synthesis,improvements made for scale-up

Maruoka et al. developed a new synthetic route to access 3,3’-disubstituted BINAM compounds which are nitrogen derivatives of popular axial chiral ligands BINOL and BINAP. Their multi step approach involves in partial hydrogenation of BINAM to H8-BINAM, 3,3’-dihalogenation, and...