Studies on organophosphorus compounds 80. Stereoselective synthesis of fused carbocyclic and isoxazoline rings via intramolecular cycloaddition of nitrile oxides derived from α-nitroalkenes

Abstract

Stereoselective condensation of alk-3-en-1-ylphosphonates with α -nitroalkenes gave the corresponding nitro compounds, which led to the stereoselective synthesis of 6-aryl-3,3a,4,5,6-pentahydrocyclopent[c]-isoxazole-5-ylphosphonates via intramolecular nitrile oxide -olefin cylco-addition in good yield. Cyclohex-2′-en-1′-ylmethylphosphonate behaves analogously.