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Regioselective Azidolysis of Epoxides in Water Using PEG-Grafted Dowex Resin
A. R. Kiasat*, R. Badri, B. Zargar, S. Sayyahi
Chamran University, Ahvaz, Iran
22 January 2009 (online)
Dowex resin grafted with poly(ethylene glycol) promoted the regioselective azidolysis of epoxides in water. Thus, the resin-bound sulfonyl chloride 2 was obtained via the reaction of Dowex resin with thionyl chloride and subsequently transformed into Dowex resin supported poly(ethylene glycol) 3 using PEG300 in dichloromethane. Azidolysis of 2,3-epoxypropyl phenyl ether was carried out with catalyst 3 in water at 100 ˚C for 0.5 h to give 2-azido-2-phenyl-1-ethanol 5 in 85% isolated yield. The azidolysis of several epoxides were examined under similar reaction conditions to afford the corresponding azidohydrin in good yield (10 examples: 2-96% isolated yield).