Construction of bicyclic systems containing an oxygen bridge by isomerization of cyclic epoxy alcohols |
| |
| Authors: | Masaru Iwakura Hiroshi Tokura Keiji Tanino |
| |
| Institution: | 1. Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-0810, Japan;2. Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan |
| |
| Abstract: | A novel method for constructing a 7-oxabicyclo2.2.1]heptane skeleton was developed. The substrates, namely cis-3,4-epoxy-1-cyclohexanol derivatives, were prepared from the corresponding 3-cyclohexen-1-ol derivatives via a stereoselective epoxidation reaction using a vanadium catalyst. Upon heating with lithium iodide in propionitrile, the cis-epoxy alcohol was transformed into the 7-oxabicyclo2.2.1]heptane derivative in high yield. The reaction proceeds through formation of a lithium alkoxide bearing an iodohydrin moiety, followed by an intramolecular SN2 reaction. |
| |
| Keywords: | Epoxide Cyclic ether Iodohydrin Isomerization |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
