The conversion of 4-oxa-5-hexenyllithiums to 4-alken-1-ols: a novel [1,4]-wittig rearrangement
作者:William F. Bailey、Lyn M.J. Zarcone
DOI:10.1016/0040-4039(91)80002-n
日期:1991.1
corresponding 3-iodoalkyl vinyl ethers (1) by low-temperature lithium - iodine exchange, rearrange in high yield to 4-alken-1-ols (4) when warmed to room temperature. This transformation, which constitutes a [1,4]-Wittig rearrangement, is mediated by 5-exo-trig closure of 2 to a (2-tetrahydrofuranyl)methyllithium (3) followed by spontaneous ring opening to give 4.
4-氧杂-5-己烯基锂(2),可以由相应的3-碘烷基乙烯基醚(1)通过低温锂-碘交换制得,并以高收率重排为4-烯-1-醇(4)。当加热到室温时。这种转变,这构成了〔1,4〕-Wittig重排,由5 -外-TRIG的闭合介导2的(2-四氢呋喃基)甲基锂(3然后自然开环),得到4。