手性胺盐催化的α,β-不饱和酮的不对称环氧化反应  

Asymmetric Epoxidation of α,β-Enones Catalyzed by Chiral Amine Salts

作　　者：王巧峰[1] 陈惠[1] 刘鹏[1] 王全军[1] 王绪国[1] 张生勇[1] 

机构地区：[1]第四军医大学药学系,西安710032

出　　处：《有机化学》2009年第10期1617-1620,共4页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20842007);陕西省自然科学基金(No.SJ08-ZT02)资助项目

摘　　要：以手性胺衍生的有机催化剂催化α,β-不饱和酮的不对称环氧化反应,考察了手性胺的结构、氧化剂的种类和溶剂对反应立体选择性的影响.结果表明金鸡纳碱衍生9-氨基(9-脱氧)表辛可宁(A6)催化α,β-不饱和酮的不对称环氧化反应时,其光学产率可达84%ee.通过共价键负载于β-环糊精的手性胺在查尔酮的不对称环氧化反应中也显示出立体诱导作用.Chiral amine salts were applied to catalyze the asymmetric epoxidation of α,β-enones. It was found that a variety of chiral amines and oxidants affected the enantioselectivity of the reaction respectively. The results showed that the optical yield reached up to 84% ee when 9-amino（9-deoxy）epicinchonine （A6） was used to catalyze the asymmetric epoxidation of α,β-unsaturated ketones. Meanwhile, the β-cyclodextrinmodified chiral amine salt also exhibited the chiral inducibility in asymmetric epoxidation of chalcone.

关 键 词：α β-不饱和酮 不对称环氧化 手性胺 金鸡纳生物碱 β-环糊精 

分 类 号：O643.32[理学—物理化学]