A Novel Synthesis of 2-Acyl Cyclic Ethers and 3-Keto Cyclic Ethers Including Spiro Cyclic Ethers via Intramolecular Ring-Opening of α,β-Epoxy Sulfoxides with Hydroxyl Group

Article abstract of DOI:10.1246/bcsj.61.2109

The α,β-epoxy sulfoxides 1 and 2 bearing a ω-oxyalkyl group were synthesized from ω-oxyalkyl carbonyl compounds and 1-chloroalkyl phenyl sulfoxide.The intramolecular ring opening of the oxirane ring of these α,β-epoxy sulfoxides, through an attack of the terminal hydroxyl group, gave 2-acyl cyclic ethers or 3-keto cyclic ethers, including spiro-type cyclic ethers.This procudure is applicable to the preparation of five- and six-membered cyclic ethers.