氮杂环卡宾催化乙酸酯和β-硅基烯酮的[4+2]环合反应:高立体选择性合成β-硅基δ-内酯  

N-Heterocyclic Carbene-Catalyzed[4+2]Annulation of Acetates and β-Silyl Enones:Highly Enantioselective Synthesis of β-Silylδ-Lactones

作　　者：张雨霞 郭京程 黄杰 付振乾 Zhang Yuxia;Guo Jingcheng;Huang Jie;Fu Zhenqian(Institute of Advanced Materials,Nanjing Tech University,Nanjing 211816;School of Chemistry and Molecular Engineering,Nanjing Tech University,Nanjing 211816)

机构地区：[1]南京工业大学先进材料研究院,南京211816 [2]南京工业大学化学与分子工程学院,南京211816

出　　处：《有机化学》2021年第11期4467-4475,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21602105)资助项目.

摘　　要：在氮杂环卡宾催化下,乙酸酯和β-硅基烯酮发生[4+2]环合反应,可高立体选择性地合成具有潜在应用价值的β-硅基δ-内酯类化合物.该方法具有底物简单易得、反应条件温和、底物普适性好和操作简单等优点,且反应规模放大10倍后也得到了优异的产率和对映体选择性.该反应产物在氢化还原反应中均呈现出优良的实验结果,可转化为降血脂药Ezetimibe.Asymmetric synthesis of chiral organosilanes with a potential application was realized by N-heterocyclic carbenecatalyzed[4+2]annulation of acetates and β-silyl enones.This strategy exhibits easy to obtain raw materials,mild reaction conditions,good substrate tolerance,simple operation and so on.Notably,excellent yield and enantioselectivity were also observed with expanding the reaction scale by 10 times.The target product showed excellent results in hydrogenation reduction.Moreover,the hypolipidemic drug ezetimibe was obtained through the synthetic transformation of the resulting products.

关 键 词：氮杂环卡宾 手性有机硅烷化合物 不对称催化 β-硅基烯酮 乙酸酯 

分 类 号：O627.41[理学—有机化学]