4-羟基香豆素与β-硝基烯烃的不对称Michael加成/环化串联反应  

Michael/cyclization tandem reaction of 4-hydroxycoumarin with β-nitroolefins

作　　者：王黎明 杨文鑫 张俊伟 金瑛 WANG Li-ming;YANG Wen-xin;ZHANG Jun-wei;JIN Ying(Department of Pharmacy,Jilin Medical University,Jilin 132013,China)

机构地区：[1]吉林医药学院药学院,吉林吉林132013

出　　处：《化学研究与应用》2022年第4期834-841,共8页Chemical Research and Application

基　　金：吉林省教育厅科学技术项目(JKH20200450KJ)资助;吉林省卫生厅创新项目(2020J074)资助;大学生创新训练项目(202013706006)资助。

摘　　要：将金鸡纳碱衍生催化剂用于有机催化4-羟基香豆素和β-硝基芳基乙烯的不对称Michael加成/环化串联反应。在0.1 mmol底物用量条件下,筛选出最佳的催化剂体系为:10 mol%催化剂1g,200 mg 3A分子筛,三氯甲烷(1 mL)为溶剂,室温反应,以60~75%的产率和最高达92%的对映选择性获得了手性二氢呋喃酮化合物。Organocatalysts of cinchona alkaloid derivatives were applied in the asymmetric Michael/cyclization reaction of 4-hydroxycoumarin with β-nitroarylethenes.Under the condition of 0.1 mmol substrate amount,the optimized conditions were determined to be 10 mol%loading catalyst 1 g with 200 mg 3A MS in CHCl;(1 mL)at room temperature.The different substituted β-nitroarylethenes were evaluated for the generality of this reaction,the desired chiral 2,3-dihydrofuro[3,2-c]coumarin compounds were obtained in 60~75%yield with up to 92%enantiomeric excess(ee).

关 键 词：金鸡纳碱衍生物 不对称Michael加成/环化串联反应 4-羟基香豆素 β-硝基芳基乙烯 

分 类 号：O621.3[理学—有机化学]