双功能[2.2]对环蕃基氮杂环卡宾催化查尔酮的不对称硼化反应的研究  

Asymmetric Boration of Chalcones Catalyzed by Bifunctional [2.2] Paracyclophane-Based N-Heterocyclic Carbene

作　　者：叶梦 申盼盼 段文增 宋淳 马玉道[1] 

机构地区：[1]山东大学化学与化工学院,济南250100 [2]聊城大学化学与化工学院,聊城252000

出　　处：《有机化学》2017年第11期2919-2928,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21372144;81473085)资助项目~~

摘　　要：为了达到无金属催化的不对称硼化反应高选择性的目的,设计并合成了基于[2.2]对环蕃的手性氮杂环卡宾前驱体.应用该双功能的卡宾催化剂实现了商业化的联硼酸频哪醇酯[B_2(pin)_2]对查尔酮的不对称加成反应,得到了高达99%收率和97%对映体选择性的有机硼化合物.研究还发现,水作为添加物在该反应中发挥关键作用.A robust chiral N-heterocyclic carbene precursor based on [2.2]paracyclophane was designed and synthesized for a highly enantioselective metal-free catalytic boration.Enantioselective 1,4-addition of a commercially available bis（pinacolato）-diboron（B_2（pin）_2） to chalcones was achieved by using the new bifunctional chiral carbene as catalyst,affording the corresponding products in up to 99% yield and 97% enantiomeric excess.Moreover,it was found that water used as the additive plays a key role in the carbene-catalyzed enantioselective boration.

关 键 词：有机催化 不对称催化 卡宾 硼化合物 [2.2]对环蕃 

分 类 号：O621.251[理学—有机化学]