基于金鸡纳碱的磺酰脲类小分子催化剂的合成及其在不对称Michael加成反应中的应用  

An Efficient Synthesis of Bifunctional Cinchona Alkaloid-based Sulfonylureas and Their Applications in Asymmetric Michael Addition

作　　者：张志平[1] 解鸿宇[1] 班树荣[1] 李青山[1] ZHANG Zhi-ping;XIE Hong-yu;BAN Shu-rong;LI Qing-shan(School of Pharmacy,Shanxi Medical University,Taiyuan 030001,China)

机构地区：[1]山西医科大学药学院

出　　处：《合成化学》2019年第11期862-866,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目((81172938);山西省自然科学基金资助项目(2015011104);山西省高等学校科技创新项目(2013118);山西医科大学科技创新基金资助项目(C01201009)

摘　　要：金鸡纳碱类衍生物广泛应用于有机小分子催化。本文采用Mitsunobu反应和磺酰基异氰酸酯的胺解,合成了4种金鸡纳碱-磺酰脲类催化剂(3a^3d),其结构经1 H NMR,13 C NMR,IR和HR-MS(ESI)表征。在优化反应条件下,3a催化硝基甲烷与查尔酮间的不对称Michael加成反应,收率71%和33%ee。Cinchona alkaloid derivatives are widely used as effective organocatalysts.In this paper four bifunctional cinchona alkaloid-based sulfonylureas(3a^3d)were prepared in very good yields(78%~86%)by Mitsunobu reaction of cinchona alkaloids and amination of isocyanate.The structures were characterized by 1 H NMR,13 C NMR,IR and HR-MS(ESI).The catalysts were evaluated in the asymmetric Michael addition of nitromethane to chalcone.Sulfonylureas 3a could facilitate the reaction with yield of 71%and 33%ee.

关 键 词：金鸡纳碱 磺酰脲 有机小分子催化 MICHAEL加成反应 合成 

分 类 号：O643.32[理学—物理化学]