Nickel(II)-Catalyzed [3 + 2] Cycloaddition of Nitrones and Allenoates to Access N-Vinylindoles and N-Vinylpyrroles.
废止
组合化学
有机化学
区域选择性
芳基
作者
Pei-Pei Xu,Jun-Yi Liao,Jia-Jie Zhang,Wei-Min Shi,Cui Liang,Gui-Fa Su,Dong-Liang Mo
出处
期刊:Organic Letters [American Chemical Society] 日期:2021-10-01卷期号:23 (19): 7482-7486被引量:1
标识
DOI:10.1021/acs.orglett.1c02695
摘要
A variety of N-vinylindoles and N-vinylpyrroles were prepared in moderate to good yields through the nickel(II)-catalyzed [3 + 2] cycloaddition of α,β-unsaturated nitrones with allenoates under mild reaction conditions. A rational mechanism for the formation of N-vinylindoles was proposed based on the 18O-labeled experiments and key intermediates detected by high-resolution mass spectrometry trace experiments. The present method highlights a nickel(II)-controlled cyclization, atom-economical reaction, broad substrate scope, good functional group tolerance, and high Z-stereoselectivity for the enamine bond.