Synthesis of C—N Axial Chirality N-Arylindoles via Pd(II)-Catalyzed Free Amine-Directed Atroposelective C—H Olefination  

作　　者：Lei Wang Wen-Kui Yuan Zhen-Kai Wang Jun Luo Tao Zhou Bing-Feng Shi 

机构地区：[1]Center of Chemistry for Frontier Technologies,Department of Chemistry,Zhejiang University,Hangzhou,Zhejiang,310027 China [2]College of Chemistry and Molecular Engineering,Zhengzhou University,Zhengzhou,Henan,450001 China [3]School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang,Henan,453007 China

出　　处：《Chinese Journal of Chemistry》2023年第21期2788-2792,共5页中国化学（英文版）

基　　金：We thank the support from National Key R&D Program of China(2022YFA1504302,2021YFF0701603);National Natural Science Foundation of China(U22A20388,92256302,21925109 for B.-F.S.,22271250 for T.Z.);Fundamental Research Funds for the Central Universities(226-2023-00115,226-2022-00224,226-2022-00175);Zhejiang Provincial NSFC(LD22B030003)。

摘　　要：Axially chiral N-arylindoles bearing a stereogenic C—N axis are unique important scaffolds in natural products,advance materials,pharmaceuticals and privileged chiral ligands or catalysts.Herein,we report the direct synthesis of C—N axially chiral N-arylindoles through a Pd-catalyzed free amine-directed atroposelective C—H olefination enabled by a spiro phosphoric acid(SPA)ligand.A wide range of enantioenriched N-aromatic amine indoles were obtained in high yields with good enantioselectivities(35 examples,up to 91%yield and up to 96%ee).The chiral products with free amine group offer an effective functional handle for down-stream diversity-oriented synthesis.

关 键 词：C-N axial chirality Free amine-directed C-H activation Chiral spiro phosphoric acids PALLADIUM Olefination Asymmetric synthesis 

分 类 号：O621.251[理学—有机化学]