Metal-free nucleophilic 7,8-dearomatization of quinolines:Spiroannulation of aminoquinoline protected amino acids  

作　　者：Zhiguo Zhang Xiyang Cao Xiaoqing Song Gang Wang Bingbing Shi Xiang Li Nana Ma Lantao Liu Guisheng Zhang 

机构地区：[1]Key Laboratory of Green Chemical Media and Reactions,Ministry of Education,Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals,NMPA Key Laboratory for Research and Evaluation of Innovative Drug,School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang 453007,China [2]The College of Chemistry and Chemical Engineering,Shangqiu Normal University,Shangqiu 476000,China

出　　处：《Chinese Chemical Letters》2023年第2期219-223,共5页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China (Nos. 22101074, 21877206, and 21772032);the 111 Project (No. D17007);Excellent Youth Foundation of Henan Scientific Committee (No. 222300420012);China Postdoctoral Science Foundation (No. 2019M660173);the Natural Science Foundation of Henan Province (No. 202300410233)。

摘　　要：Atom-and step-economy in IBX assisted diversity-oriented synthesis is achieved with a versatile AQ auxiliary α-amino acid analogs offering rapid access to polycyclic spiro-quinolines featuring a quaternary stereocenter in 20%–91% yields under mild conditions via 7,8-dearomatization of quinolines. Free of a preinstalled activation group is highlight of this intramolecular oxidation spiroannulation tandem reaction. This type of N-heterospirocycles, traditionally difficult to access, may open the door to a potentially interest scaffold for synthetic and medicinal chemistry.

关 键 词：DEAROMATIZATION Spiroannulation Aminoquinoline Amino acids Hypervalent iodine reagents 

分 类 号：TQ460.1[化学工程—制药化工]