Aqueous-mediated ring opening of epoxides with oximes: A rapid entry into β-hydroxy oxime O-ethers as potential β-adrenergic blocking agents

Article abstract of DOI:10.1055/s-2008-1067122

Novel β-hydroxy oxime O-ethers, as potential β-adrener-gic blocking agents, were synthesized from the aqueous-mediated (H₂O - DMSO, 7:3) O-alkylation of oximes with epoxides in the presence of potassium hydroxide at room temperature. The O-alkylation was regioselective and (E)-oxime ethers were the main products. The results of quantum mechanical studies used to rationalize the experimental outcomes are discussed. Thieme Stuttgart.