Syn -Stereoselective C3-Spirocyclization and C2-Amination of 3-(2-Isocyanoethyl)indole Using C , N -Cyclic Azomethine Imines

作者：Wenbin Cao, Jiandong Zhang, Mengmeng Xu, Huawei Liu, Haiyan Li, Xiaoping Xu, Shun‐Jun Ji · 发表于：Organic Letters · 年份：2022 · DOI：10.1021/acs.orglett.2c01736 · 被引用次数：18 · 研究领域：Asymmetric Synthesis and Catalysis、Synthesis and Catalytic Reactions、Chemical Synthesis and Analysis

By utilizing an underexplored reaction mode of C, N -cyclic azomethine imines, a catalyst-free [1+2+3] cycloaddition/N–N bond cleavage sequential reaction for accessing spiroindolines with syn -stereoselectivity was developed. On the basis of experimental results and DFT calculations, peroxide and ethereal solvent were identified to trigger the hydrogen abstraction of the unstable [1+2+3] cycloaddition adducts, followed by homolytic cleavage of the N–N bond and hydrogen absorption.