Enantioselective[2+2]cycloaddition of 1,2-dihydroquinolines with 3-olefinic oxindoles via Brønsted acid catalysis  

作　　者：Biao Wang Xiao Yan Han Zhong Qin Ouyang Xu Tian 

机构地区：[1]Key Laboratory of Molecular Target&Clinical Pharmacology and the State Key Laboratory of Respiratory Disease,School of Pharmaceutical Sciences&the Fifth Affiliated Hospital,Guangzhou Medical University,Xinzao,Panyu District,Guangzhou,511436,China [2]College of Pharmacy,Third Military Medical University,Chongqing,400038,China

出　　处：《Organic Chemistry Frontiers》2022年第6期1621-1627,共7页有机化学前沿（英文）

基　　金：support from the NSFC(21702035);the National Key Research and Development Program of China(Grant No.2018YFA0507900);the Pearl River Talents Recruitment Program of Guangdong Province(2017GC010600);the Science and Technology Program of Guangzhou(201804010455)is greatly appreciated.

摘　　要：Mutually complementary regiodivergent Brønsted acid-catalyzed atom-economical[2+2]cycloadditionand ene reactions of 1,2-dihydroquinolines with 3-olefinic oxindoles are reported.In the presence of achiral phosphoramide catalyst,the[2+2]cycloaddition affords products with four contiguous stereocenters in good to excellent yields(up to 95%)and with high stereoselectivities(up to>99%ee,>20:1 dr).Conversely,with a stronger Brønsted acid,the trifluoromethanesulfonic acid catalyst leads to ene reactionproducts in high yields(up to 77%).Furthermore,the mechanisms of the reactions are discussed based oncontrol experiments and DFT calculations.

关 键 词：catalyst CYCLOADDITION INDOLE 

分 类 号：O64[理学—物理化学]