Tetrahedron

Solvent-free direct regioselective ring opening of epoxides with imidazoles

R Torregrosa, IM Pastor, M Yus

Index: Torregrosa, Rosario; Pastor, Isidro M.; Yus, Miguel Tetrahedron, 2007 , vol. 63, # 2 p. 469 - 473

Full Text: HTML

Citation Number: 50

Abstract

The reaction of different epoxides with commercially available imidazole at 60° C leads to the formation of the corresponding 1-(β-hydroxyalkyl) imidazoles in a regioselective manner. When the reaction is applied to a chiral epoxide [(R)-styrene oxide], the expected chiral alcohol is isolated with the same enantiomeric excess. The use of benzimidazole as the heterocyclic component in the same process also allows the simple preparation of the ...