化学
烯醇
产量(工程)
薗头偶联反应
Negishi偶联反应
有机化学
组合化学
催化作用
钯
冶金
材料科学
作者
Hidefumi Nakatsuji,Kanako Ueno,Tomonori Misaki,Yoo Tanabe
出处
期刊:Organic Letters
[American Chemical Society]
日期:2008-05-09
卷期号:10 (11): 2131-2134
被引量:70
摘要
We have developed a general, robust, and cost-effective method for the (E)- or (Z)-stereocomplementary enol tosylation of β-ketoesters using TsCl−N-methylimidazole (NMI)−Et3N or LiOH. TsCl coupled with NMI formed a highly reactive N-sulfonylammonium intermediate. Stereocongested secondary alcohols were smoothly sulfonylated using Ts(Ms)Cl−NMI−Et3N. β-Ketoesters underwent (E)-selective tosylation using TsCl−NMI−Et3N and (Z)-selective tosylation using TsCl−NMI−LiOH (total of 23 examples; 60%−99% yield). Stereoretentive Negishi and Sonogashira couplings using enol tosylates proceeded successfully to give trisubstituted α,β-unsaturated esters.
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