钛/樟脑烷二醇催化的不对称硫醚氧化反应研究  

Study on the Titanium/Camphanediol-catalyzed Enantioselective Sulfoxidation Reaction

作　　者：张颂[1] 唐红艳[1] 刘洋[1] 董俊宇[1] 高珊[1] 杨治仁[1] 王河清[1] 曾庆乐[1] 

机构地区：[1]成都理工大学材料与化学化工学院化工与制药系,四川成都610059

出　　处：《合成化学》2010年第2期206-209,共4页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(20672088)

摘　　要：以天然樟脑为原料,经5步反应合成了手性樟脑烷二醇(endo-1),实验发现endo-1在放置过程中可完全转化为exo-1,其结构经1H NMR,13C NMR和ESI-MS表征。以exo-1为配体,研究了不同氧化剂及其用量对钛催化的不对称硫醚氧化反应的影响。结果表明,用枯烯过氧化氢作氧化剂时,亚砜主产物构型出现逆转,而用叔丁基过氧化氢则不会。Chiral camphanediol（endo-1） was synthesized from natural camphor by a five-step reaction. The complete conversion of endo-1 to exo-1 was found during storage. The structure was characterized by 1^H NMR, 13^C NMR and ESI-MS. Using exo-1 as ligand, the effects of various oxidants and their amounts on titanium-catalyzed enantioselective sulfoxidation were investigated. The results showed that the configuration of the product sulfoxide was reversed using eumene hydroperoxide as the oxidant, but it was not using t-butyl hydroperoxide as the oxidant.

关 键 词：D-樟脑 樟脑烷二醇 钛催化 不对称硫醚氧化 构型逆转 合成 

分 类 号：O623.413[理学—有机化学] O623.83[理学—化学]