基于甜菊糖苷骨架的手性叔胺-方酰胺催化剂的合成及催化性能研究  

Synthesis and catalytic performance of chiral tertiary amine-squaramide catalyst based on stevioside skeleton

作　　者：刘志景 马志伟 刘俊桃 王川川 陶京朝[2] LIU Zhi-jing;MA Zhi-wei;LIU Jun-tao;WANG Chuan-chuan;TAO Jing-chao(Faculty of Science,Henan University of Animal Husbandry and Economy,Zhengzhou 450046,China;College of Chemistry,Zhengzhou University,Zhengzhou 450001,China)

机构地区：[1]河南牧业经济学院理学部,河南郑州450046 [2]郑州大学化学学院,河南郑州450001

出　　处：《化学研究与应用》2022年第7期1662-1666,共5页Chemical Research and Application

基　　金：河南省自然科学基金项目(202300410188)资助;河南省高等学校青年骨干教师培养计划项目(2021GGJS173)资助;河南牧业经济学院科研项目(XKYCXJJ2020002,2018HNUAHEDF014)资助。

摘　　要：以天然产物异斯特维醇为原料,合成了一种新型叔胺-方酰胺有机催化剂,通过^(1)HNMR、^(13)C NMR、IR、HR-MS对其结构进行了表征。将该催化剂用于1,3-环己二酮与β,γ-不饱和α-酮酯的不对称Michael加成反应中,在最优化的反应条件下,催化剂用量仅为1 mol%,合成了一系列手性双环化合物,最高产率达到95%,最高ee值达到95%。A novel tertiary amine-squaramide organocatalyst was synthesized from natural product isosteviol,and its structure was characterized by ^(1)HNMR,^(13)C NMR,IR and HR-MS.The catalyst was applied into the asymmetric Michael addition of 1,3-cyclohexanediones toβ,γ-unsaturatedα-ketoesters.Under the optimal reaction conditions,the amount of catalyst was only 1 mol%,and a series of chiral bicyclic compounds were synthesized in high yields(up to 95%)with excellent enantioselectivities(up to 95%ee).

关 键 词：MICHAEL加成 有机催化 叔胺-方酰胺 异斯特维醇衍生物 

分 类 号：O621.3[理学—有机化学]