Stereochemical Features Making Deoxycholic Acid Derived <i>tropos</i> Biphenylphosphites Efficient Chiral Ligands for Rhodium: The Asymmetric Hydrogenation of Dimethylitaconate as a Case Study

Abstract

Different deoxycholic acid derived biphenylphosphites, whose tropos nature was ascertained by NMR and CD measurements, were used in the rhodium-catalyzed asymmetric hydrogenation of dimethylitaconate achieving enantiomeric excesses up to 91%. The comparison of these results to those obtained using the corresponding atropoisomeric binaphthyl analogues, together with NMR and CD measurements on the rhodium complexes of some phosphites, allowed us to shed light on the nature of the active catalytic species and on the asymmetric induction process and hence to recognize the most appropriate stereochemical features to reach good levels of enantioselectivity.