新型表面活性剂类硫脲高效催化硝基烯烃的不对称Michael加成(英文)  

Efficient enantioselective michael addition of nitroalkenes catalyzed by a new surfactant-type thiourea organocatalyst in water

作　　者：张红英[1,2] 陈仲清[1] 颜雪明[1] 

机构地区：[1]南华大学化工学院,湖南衡阳421001 [2]衡阳财经工业职业技术学院材料系,湖南衡阳421002

出　　处：《暨南大学学报（自然科学与医学版）》2014年第6期525-531,542,共8页Journal of Jinan University(Natural Science & Medicine Edition)

基　　金：Education Scientific Research Project of Hunan Province(No.14C0157;11C1084)

摘　　要：由N-BOC-胺甲基吡咯烷和异硫氰酸盐反应合成了-种新型结构的硫脲分子,将该具有表面活性剂类型的硫脲分子用作有机催化剂来催化硝基烯烃的不对称Michael加成,条件实验探索结果表明,最优的实验条件是,10mol%催化剂,10mol%的苯甲酸作为添加剂,用水做溶剂以及在室温反应温度.在该最优条件下,可以非常顺利地实现各种硝基烯烃与各类醛和酮的Michael加成,得到较高的收率（76% ～97%）,良好的几何选择性（顺∶反=82∶18～99∶1）以及对映选择性（ee值达到97%）.A new thiourea structure was synthesized from the reaction of N-BOC-aminomethylpyrroli-dine and isothiocyanate.This surfactant-type thiourea was used as organocatalyst to catalyze Michael reac-tion of nitroalkenes,and the ondition experiment showed that the optimized reaction should be in the presence10 mol% organocatalyst,using 10 mol% PhCOOH as additive,use water as solvent and at room temperature.Under this optimal conditions,various nitroalkenes could undergo Michael addition smoothly with other ketones or aldehydes at room temperature for 6 -24 hr,giving the desired adducts in good yields (76% ~97%)with high diastereoselectivities (syn∶anti =82∶18 ~99∶1 )and enantioselectivities (up to 97% ee).

关 键 词：有机催化剂 不对称催化 不对称MICHAEL加成 表面活性剂类催化剂 

分 类 号：TQ032.42[化学工程] O624.42[理学—有机化学]