Electrolytic partial fluorination of organic compounds.71. Highly diastereoselective anodic fluorination of sulfides having oxygen-containing heterocyclic groups |
| |
Authors: | Suzuki Katsutoshi Fuchigami Toshio |
| |
Affiliation: | Department of Electronic Chemistry, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan. |
| |
Abstract: | Diastereoselective anodic fluorination of sulfides having various oxygen-containing heterocyclic substituents such as 2-furanyl, 1,3-dioxolanyl, 2,2-dimethyl-1,3-dioxolanyl, 2-spirocyclohexyl-1,3-dioxolanyl, 2-spiroadamantyl-1,3-dixolanyl, and 1,3-dioxolanonyl groups at the beta-position was comparatively studied. Among the oxygen-containing heterocyclic substituents, the 2-spirocyclohexyl-1,3-dioxolanyl group gave the best diastereoselectivity (80% de). The diastereoselectivity was also affected by supporting fluoride salts and solvents. Chemical fluorination using selectfluor resulted in much lower diastereoselectivity and extremely poor yield. The fluorinated products were readily converted into the corresponding fluorinated diol in good yields by acidic hydrolysis. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|