Preparation and characterization of α-fluorinated-γ-aminophosphonates

Herein we would like to present a synthetic approach to series of alpha-fluorinated-gamma-aminophosphonates, which were prepared by hydrogenolysis of (E)-alpha-fluorovinylphosphonates. The reaction conditions of hydrogenolysis in the presence of palladium on carbon has been optimized. After conversion of aminophosphonates to their oxalte salts, the absolute configuration of the main diastereoisomer has been determined by X-ray analysis. alpha-Fluorinated-gamma-aminophosphonates can be used as convenient precursors (building blocks) in the preparation of medicinally important analogues. As an example preparation of dipeptide analogues of alpha-fluorinated-gamma-aminophosphonates was described. (C) 2014 Elsevier B.V. All rights reserved.