Practical regioselective synthetic method for (E)-enol ether
作者:Hyeung-geun Park、Dong-Hwa Kim、Misuk You、Mi-kyoung Park、Sang-sup Jew
DOI:10.1016/s0040-4039(00)00603-1
日期:2000.6
A new practical and highly regioselective synthetic method for (E)-enol ether is reported. (E)-enol ethers (E:Z=93:7–99:1) were prepared from the corresponding enolacetates (E:Z≅3:1) in two steps by bromination and anti-elimination of α-bromodialkylacetal via metal halogen exchange.
The 17ONMRspectra of a number of alkyl‐ and phenyl‐substituted divinyl ethers were recorded in CDCl3 solution. The relationship between chemical shift and the number, nature and position of substituents was explored. The shift values, falling in the range δ 100–140 ppm, were found to be remarkably insensitive to the electronic and stereochemical effects of substituents. The narrow range of chemical