Base-catalyzed stereoselective isomerization of electron-deficient propargylic alcohols to E-enones
Base-catalyzed stereoselective isomerization of electron-deficient propargylic alcohols to E-enones
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DOI：
10.1021/jo060304p
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发表时间：
2006-08-04
影响因子：
3.6
通讯作者：
Koide, Kazunori
中科院分区：
文献类型：
--
作者：
Sonye, John P.;Koide, Kazunori
我们开发了高度立体选择性的方法，可在温和条件下将缺电子炔丙醇异构化为 E-烯酮（EWG = 吸电子基团）。在我们筛选的弱碱中，催化 (10-20 mol%) 1,4-二氮杂双环[2.2.2]辛烷 (DABCO) 在大多数情况下被发现是有效的。当底物与酰胺缀合时，乙酸钠的添加催化异构化。
We have developed highly stereoselective methods to isomerize electron-deficient propargylic alcohols to E-enones under mild conditions ( EWG = electron-withdrawing group). Among weak bases we screened, catalytic ( 10-20 mol %) 1,4-diazabicyclo[ 2.2.2] octane ( DABCO) was found to be effective in most cases. When the substrate is conjugated with an amide, the addition of sodium acetate catalyzed the isomerization.