手性特窗酸类化合物的合成  

Synthesis of Chiral Tetronic Acids Compounds

作　　者：罗年华[1] 王勇[1] 郑大贵[1] 张小兰[1] 胡昕[1] 朱顺桃 LUO Nian-hua;WANG Yong;ZHENG Da-gui;ZHANG Xiao-lan;HU Xin;ZHU Shun-tao(Key Laboratory of Applied Organic Chemistry,Higher Institutions of Jiangxi Province,Shangrao Normal University,Shangrao 334001,China)

机构地区：[1]上饶师范学院江西省普通高校应用有机化学重点实验室,江西上饶334001

出　　处：《合成化学》2018年第9期654-660,共7页Chinese Journal of Synthetic Chemistry

基　　金：江西省自然科学基金资助项目(20161BAB213059);江西省教育厅科技计划项目(GJJ151052)

摘　　要：考察了一系列手性吡咯烷叔胺硫脲催化剂对4-氯代乙酰乙酸乙酯与亚胺的不对称Mannich/Cyclization串联反应的催化性能,合成了一系列具有潜在生物活性的手性特窗酸类衍生物,产率62%~92%,对映选择性68%~96%,产物结构经~1H NMR,^(13)C NMR,IR和HR-MS确证。并对反应条件进行了优化,对反应机理进行了推测。The asymmetric Mannich/Cyclization cascade reaction of ethyl 4-chloro-3-oxobutanoate with imines catalyzed by a series of chiral pyrrolidine-based thiourea-tertiary amines were investigated. A series of chiral tetronic acids derivatives with potential biological activities were synthesized in 62%～92% yields and 68%～96% ee values. The structures were confirmed by 1 H NMR, 13 C NMR, IR and HR-MS. The reaction conditions were optimized and the catalytic mechanism was proposed.

关 键 词：4-氯代乙酰乙酸乙酯 亚胺 吡咯烷叔胺硫脲 催化 MANNICH反应 串联反应 特窗酸 合成 

分 类 号：O626.1[理学—有机化学]