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
作者:Tsuyoshi Satoh、Ken-ichi Iwamoto、Atsushi Sugimoto、Koji Yamakawa
DOI:10.1246/bcsj.61.2109
日期:1988.6
The α,β-epoxy sulfoxides 1 and 2 bearing 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 procedure is applicable to the
带有ω-氧烷基的α,β-环氧亚砜1和2是由ω-氧烷基羰基化合物和1-氯烷基苯基亚砜合成的。这些 α,β-环氧亚砜的环氧乙烷环的分子内开环,通过末端羟基的攻击,得到 2-酰基环醚或 3-酮环醚,包括螺型环醚。该程序适用于五元和六元环醚的制备。