钯催化环丁酮与乙炔基苯胺之间的对映选择性串联C-C键活化/Cacchi反应
Pd-Catalyzed Enantioselective Tandem C-C Bond Activation/Cacchi Reaction between Cyclobutanones and -Ethynylanilines.
作者信息
Yang Wan-Chun, Chen Xiao-Bing, Song Kun-Long, Wu Bin, Gan Wan-Er, Zheng Zhan-Jiang, Cao Jian, Xu Li-Wen
机构信息
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute and Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P.R. China.
出版信息
Org Lett. 2021 Feb 19;23(4):1309-1314. doi: 10.1021/acs.orglett.0c04297. Epub 2021 Feb 4.
A palladium-catalyzed asymmetric tandem C-C bond activation/Cacchi reaction between cyclobutanones and -ethynylanilines was reported. The transient chiral σ-alkylpalladium species generated via enantioselective C(sp)-C(sp) bond activation of cyclobutanones promotes cyclization of -ethynylanilines, leading to one-carbon-tethered chiral indanone-substituted indoles. Two C-C bonds and one C-N bond are created with concomitant formation of an all-carbon quaternary stereocenter. Furthermore, a chiral C2-aryl axis can be created in 2,3-disubstituted indole moiety, leading to indanone-substituted indoles with both central and axial stereogenic elements.
报道了一种钯催化的环丁酮与乙炔基苯胺之间的不对称串联C-C键活化/Cacchi反应。通过环丁酮的对映选择性C(sp)-C(sp)键活化生成的瞬态手性σ-烷基钯物种促进了乙炔基苯胺的环化，生成了单碳连接的手性茚满酮取代的吲哚。同时形成了两个C-C键和一个C-N键，并伴随着一个全碳季碳立体中心的形成。此外，在2,3-二取代的吲哚部分可以产生一个手性C2-芳基轴，从而得到同时具有中心和轴向立体ogenic元素的茚满酮取代的吲哚。
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