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 

机构地区：[1]State Key Laboratory of Green Pesticide,Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education,Guizhou University,Guiyang 550025,China [2]School of Chemistry,Chemical Engineering,and Biotechnology,Nanyang Technological University,Singapore 637371,Singapore

出　　处：《Science China Chemistry》2024年第7期2199-2205,共7页中国科学（化学英文版）

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([2016]5649);the Science and Technology Department of Guizhou Province(Qiankehe-jichu-ZK[2024]-030,zhongdian024,[2018]2802,[2019]1020,QKHJC-ZK[2022]-455);the Program of Introducing Talents of Discipline to Universities of China(111 Program,D20023)at Guizhou University。

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 science.While 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 challenge.In particular,there are limited studies on the enantioselective seleno-Michael addition reactions to access chiral selenium functional molecules.Here,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 enantioselectivities.The choice of a weak inorganic base was pivotal to suppressing the unproductive racemization and decomposition of the selenium products.Notably,the catalytically generated chiral selenium-containing heterocyclic products feature remarkable antimicrobial activities that could serve as promising lead scaffolds for further agrochemical development.

关 键 词：seleno-Michael addition ORGANOCATALYSIS N-heterocyclic carbene seleno-heterocycles antimicrobial activity 

分 类 号：O627.61[理学—有机化学]