三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应  

Triethylamine-Catalyzed Cascade Reaction of γ-Hydroxy-α,β-unsaturated Ketones with Trifluoromethyl Ketones via Hemiketal Intermediates

作　　者：马海 于广浩 隋峰[1] 杨米一 刘丽[1] 李慧杰 李峰[2] 赵庆贺[1] Hai Ma;Guanghao Yu;Feng Sui;Miyi Yang;Li Liu;Huijie Li;Feng Li;Qinghe Zhao(Institute of Chinese Materia Medica,China Academy of Chinese Medical Sciences,Bejing 100700;College of Chemistry and Chemical Engineering,Shangqiu Normal University,Shangqiu,Henan 476000)

机构地区：[1]中国中医科学院中药研究所,北京100700 [2]商丘师范学院化学化工学院药物绿色合成河南省工程实验室,河南商丘476000

出　　处：《有机化学》2021年第4期1614-1621,共8页Chinese Journal of Organic Chemistry

基　　金：中国中医科学院自主研发(No.ZZ0908028)资助项目。

摘　　要：研究了三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应,以高收率以及适中的非对映选择性得到了一系列产物.在手性奎宁衍生的双功能硫脲催化剂存在下,该反应以92%的收率以及96%的立体选择性得到目标产物.Et3N-catalyzed cascade reaction of trifluoromethyl ketones and γ-hydroxy-α,β-unsaturated ketones via hemiketal intermediate is investigated.The adducts could be easily obtained in good to excellent yields with moderate diastereoselectivities.The reaction proceeded smoothly to give the desired product in 92%yield and with 96%ee in the presence of a glycosyl and quinidine-based bifunctional chiral thiourea catalyst.

关 键 词：γ-羟基-α β-不饱和酮 三氟甲基酮 1 3-二噁烷衍生物 手性硫脲 

分 类 号：O621.251[理学—有机化学]