Synthesis and characterization of privileged monodentate phosphoramidite ligands and chiral brønsted acids derived from D-mannitol

Abstract

The synthesis of several novel chiral phosphoramidite ligands (L1-L8) with C 2 symmetric, pseudo C 2 symmetric secondary amines and chiral Brønsted acids 1a,b has been achieved. These chiral auxiliaries were obtained from commercially available D-mannitol, and secondary amines in moderate to excellent yields. Excellent diastereoselectivites of ten chiral auxiliaries were obtained. The chiral phosphoramidite ligands and chiral Brønsted acids were fully characterized by spectroscopic methods. © 2012 by the authors.