Carbene-catalyzed enantioselective seleno-Michael addition as access to antimicrobial active Se-containing heterocycles

作     者：Hongyan Long Sha Zhao Chunyan Jian Xiuli Wu Fengfei Lu Minghong Liao Fengrui Che Xingxing Wu Yonggui Robin Chi 

作者机构：State Key Laboratory of Green PesticideKey Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of ChemistryChemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore 

出 版 物：《Science China Chemistry》 (中国科学（化学英文版）)

年 卷 期：2024年第67卷第7期

页      面：2199-2205页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：supported by the National Natural Science Foundation of China(21732002,22061007,22071036,22207022) the Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules the National Natural Science Fund for Excellent Young Scientists Fund Program(Overseas)-YQHW the starting grant of Guizhou University((2022)47)) the Department of Education,Guizhou Province(Qianjiaohe KY number(2020)004) the Department of Education of Guizhou Province(QJJ(2022)205) the 10 Talent Plan(Shicengci)of Guizhou Province(5649) the Science and Technology Department of Guizhou Province(Qiankehe-jichu-ZK-030,zhongdian024,2802,1020,QKHJC-ZK-455) the Program of Introducing Talents of Discipline to Universities of China(111 Program,D20023)at Guizhou University 

主　　题：seleno-Michael addition organocatalysis N-heterocyclic carbene seleno-heterocycles antimicrobial activity 

摘      要：Organoseleniums exhibit a diverse set of biological activities that are pivotal for drug discovery and are widely explored in synthetic chemistry and material *** many transformations have been developed for non-enantioselective C–Se bond formations,the catalyst-controlled stereoselective preparation of chiral organoseleniums continues to be of considerable *** particular,there are limited studies on the enantioselective seleno-Michael addition reactions to access chiral selenium functional ***,we disclose a carbene-catalyzed highly enantioselective nucleophilic C–Se bond construction through formal[3+3]annulations between selenocarboxamides and bromoenals,affording seleno-thiazinone products with good yields and excellent *** choice of a weak inorganic base was pivotal to suppressing the unproductive racemization and decomposition of the selenium ***,the catalytically generated chiral selenium-containing heterocyclic products feature remarkable antimicrobial activities that could serve as promising lead scaffolds for further agrochemical development.