Enantiomeric O,O-dimenthyl α-iminotrifluoroethylphosphonates: Novel chiral building blocks in asymmetric synthesis of α-trifluoromethylated α-aminophosphonic acid derivatives

Abstract

Based on reaction of (+)- or (-)-dimenthyl phosphite with trifluoroacetonitrile the synthesis of optically active O,O-dimenthyl α-iminotrifluoroethylphosphonates was developed. The synthetic potential of these novel chiral synthons was demonstrated by their easy diastereoselective functionalization (hydrogenation, proline-catalyzed Mannich reaction with acetone, aza-Henry reaction, aminoalkylation of electron-rich heterocycles) to afford optically active compounds bearing biorelevant (α-trifluoromethyl-α-amino)methylphosphonic residue.