A New Saddle-Shaped Aza Analog of Tetraphenylene: Atroposelective Synthesis and Application as a Chiral Acylating Reagent  

作　　者：Yu Luo Sidi Cheng Yan Peng Xilong Wang Jing Li Chunfang Gan Shuang Luo Qiang Zhu 

机构地区：[1]State Key Laboratory of Respiratory Disease,Guangzhou Institutes of Biomedicine and Health,Chinese Academy of Sciences,Guangzhou 510530 [2]University of Chinese Academy of Sciences,Shijingshan District,Beijing 100049 [3]Guangxi Key Laboratory of Natural Polymer Chemistry and Physics,College of Chemistry and Materials,Nanning Normal University,Nanning 530001 [4]Bioland Laboratory(Guangzhou Regenerative Medicine and Health Guangdong Laboratory),Guangzhou 510005

出　　处：《CCS Chemistry》2022年第9期2897-2905,共9页中国化学会会刊（英文）

基　　金：the National Natural Science Foundation of China(nos.21772198,21871268,and 22071250);the Frontier Research Program of Bioland Laboratory(Guangzhou Regenerative Medicine and Health Guangdong Laboratory)(no.2018GRZ110105017);the Natural Science Foundation of Guangdong Province of China(no.2020A1515011428);the“BAGUI Scholar”Program of Guangxi Province of China,and SKLRD Open Project(no.SKLRD-Z-202014)for financial support;the Guangzhou Branch of the Supercomputing Center of CAS for support.

摘　　要：(Z)-7-Aryl-5-acyldibenzo[e,g][1,4]diazocin-6(5H)-one,a unique saddle-shaped bridged biaryl containing synchronized aryl–aryl and N-aryl stereogenic axes,was constructed for the first time in good yields with up to 96%enantiomeric excess(ee).The threecomponent coupling reaction,involving aryl iodide,2,2′-diisocyano-1,1′-biphenyl,and carboxylate,constructs the eight-membered ring in an atroposelective manner through palladium-catalyzed double isocyanide insertion followed by C–Obond formation during reductive elimination and amide formation after acyl transfer.

关 键 词：diazocin tetraphenylene analog atroposelective synthesis double isocyanide insertion palladium catalysis 

分 类 号：O62[理学—有机化学]