An improved preparation of alpha-fluorinated propargylphosphonates and thesolid phase synthesis of alpha-hydroxy-gamma-TIPS propargylphosphonate ester

Diethyl-3-triisopropylsilyl-1-propynephosphonate was fluorinated using NFSI to give the corresponding monofluoroderivative in good yield. The synthesi s of diethyl-l. 1w-difluoro-3-triisopropylsilylpropynephosphate was efficie ntly achieved following Burton's methodology using CuCl/Cd to promote the c oupling reaction of diethyl bromodifluoromethylphosphonate with the corresp onding alkynyl iodide. Although the solid phase synthesis of alpha -hydroxy -gamma -TIPS propargylphosphonate ester was carried out successfully, its f luorination - using DAST - failed. (C) 2001 Elsevier Science B.V. All right s reserved.