Stereoselective construction of azepine-containing bridged scaffolds via organocata-lytic bicyclization of yne-allenone esters with nitrones  

作　　者：Meng-Fan Li Shao-Qing Shi Ting Xu Qian Zhang Wen-Juan Hao Shu-Liang Wang Jianyi Wang Shu-Jiang Tu Bo Jiang 

机构地区：[1]School of Chemistry and Materials Science and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials,Jiangsu Normal University,Xuzhou 221116,China [2]Medical College,Guangxi University,Nanning,530004,China

出　　处：《Chinese Chemical Letters》2023年第4期309-312,共4页中国化学快报（英文版）

基　　金：financial support from the National Natural Science Foundation of China (Nos. 21871112 and 21971090)。

摘　　要：A new organocatalytic double annulation cascade involving scission/recombination of N-O bonds of nitrones is reported for the first time, and used to produce a range of hitherto unprecedented tricyclic bridged-fused benzo[d]azepines bearing three stereogenic centers with moderate to good yields and complete diastereoselectivity. A quinine-catalyzed reaction of yne–allenone esters with nitrones worked well and provided a convergent and regioselective pathway to access these three-dimensional scaffolds from the planar conjugated system. Density functional theory(DFT) calculations have been applied to understand the key process for forming diradical intermediates.

关 键 词：BICYCLIZATION DIASTEREOSELECTIVITY Organocatalysis Bridged heterocycles YNE-allenone esters NITRONES 

分 类 号：O621.251[理学—有机化学]