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 

作者机构：Key Laboratory of Molecular Target&Clinical Pharmacology and the State Key Laboratory of Respiratory DiseaseSchool of Pharmaceutical Sciences&the Fifth Affiliated HospitalGuangzhou Medical UniversityXinzaoPanyu DistrictGuangzhou511436China College of PharmacyThird Military Medical UniversityChongqing400038China 

出 版 物：《Organic Chemistry Frontiers》 (有机化学前沿（英文）)

年 卷 期：2022年第9卷第6期

页      面：1621-1627页

核心收录：

学科分类：07[理学] 070304[理学-物理化学(含∶化学物理)] 0703[理学-化学] 

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. 

主　　题：catalyst cycloaddition indole 

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 to99%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.