Solid-phase Synthesis of Cycloalkylphosphonates Using Polymer-supported Phenylsulfonylmethylphosphonates
【摘要】：正Solid-phase organic synthesis (SPOS) enjoys several advantages over solution-phase synthesis such as easy manipulation and purification of the organic products greatly simplified through the use of polymer-bound reagents. Phosphonate derivatives are of importance in organic chemistry because of their utility as intermediates for the synthesis of alkene derivatives by the Horner-Wadsworth-Emmons condensation and in the fields of pharmaceutical and agrochemical owing to their biological activities. Solution-phase synthetic methods for cycloalkylphosphonates are well documented, however, to our knowledge, they have not been prepared via SPOS. In continuation of our interest in SOPS with sulfone linker, we herein wish to report the further extension of this sulfone-based chemistry to a convenient, traceless solid-phase synthesis of cycloalkylphosphonates in good yields (82%-90%) and with high purity (92% by HPLC analysis) by using polystyrene-supported phenylsulfonyl-methylphosphonates.