结构简单的4-羟基脯氨酰胺高效催化醛和硝基烯不对称迈克尔加成反应  

Structurally Simplified 4-Hydroxyprolinamide for Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroolefins

作　　者：成燕琴 黎卓熹 王有娣 徐娟娟 卞证 CHENG Yan-Qin;LI Zhuo-Xi;WANG You-Di;XU Juan-Juan;BIAN Zheng(School of Pharmacy,Guangzhou Xinhua University,Guangzhou 510520,China;Key Laboratory of Polyoxometalate Science of the Ministry of Education,Faculty of Chemistry,Northeast Normal University,Changchun 130024,China)

机构地区：[1]广州新华学院药学院,广州510520 [2]东北师范大学化学学院,多酸科学教育部重点实验室,长春130024

出　　处：《应用化学》2023年第1期146-154,共9页Chinese Journal of Applied Chemistry

基　　金：广东省普通高校特色创新项目(Nos.2018KTSCX318,2020KTSCX200)资助。

摘　　要：开发了两种结构简单的反式-4-羟基-L-脯氨酰胺有机小分子催化剂,用于高效催化不对称迈克尔加成反应。在醛和硝基烯的不对称迈克尔加成反应中,以(S)-1,1’-联-2-萘酚为协同催化剂,对两种脯氨酰胺衍生物的催化活性进行研究,发现催化剂摩尔分数仅为0.5%~1%时,产物的收率最高可达96%,非对映和对映选择性值最高可达99/1和99%。该方法为开发低成本、高效率的不对称迈克尔加成反应有机催化剂体系提供了简单易行的选择。The structurally simplified trans-4-hydroxy-L-prolinamide derivatives are prepared as the efficient organocatalysts for Michael-type asymmetric reactions.Their catalytic behaviors are evaluated in the asymmetric Michael addition of aldehydes to nitroolefins with(S)-1,1’-bi-2-naphthol as the co-catalyst.Excellent diastereoand enantioselectivities(respectively up to>99/1 and 99%),as well as high yields(up to 96%)are achieved even at the catalyst loading of as low as 0.5%~1%(molar percent).This study provides a facile method to develop the low-cost and highly efficient organocatalyst system for the asymmetric Michael addition reactions.

关 键 词：不对称催化 4-羟基-L-脯氨酰胺 (S)-1 1’-联-2-萘酚 迈克尔加成 

分 类 号：O624.6[理学—有机化学]