Methyl 3‐substituted‐isoxazole‐5‐ carboxylates syntheses on solid supports via wang resin‐bound 2,3‐dibromopropionate

A novel Wang resin‐bound 2,3‐dibromopropionate reagent has been developed and used as a potential dipolarophile for the facile preparation of methyl 3‐substituted‐isoxazole‐5‐carboxylates through triethylamine, promoting a sequence of reactions involving the in situ generation of 2‐bromoacrylate resin and nitrile oxide, regioselective 1,3‐dipolar cycloaddition, and loss of hydrogen bromide in one pot, and then cleavage from the resin with sodium methoxide. The advantages of this method include simple operation and mild conditions with good yield and high purity of the products. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:444–448, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21035