Syn-Stereoselective C3-Spirocyclization and C2-Amination of 3‑(2- Isocyanoethyl)indole Using C,N‑Cyclic Azomethine Imines
Wen-Bin Cao1, Jian-Dong Zhang1, Meng-Meng Xu1, Hua-Wei Liu1, Hai-Yan Li2, Xiao-Ping Xu1,3,*（徐小平）, and Shun-Jun Ji1,4,*（纪顺俊）
1 Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, People’s Republic of China
2 Analysis and Testing Center, Soochow University, Suzhou 215123, People’s Republic of China
3 Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, People’s Republic of China; Innovation Center for Chemical Science, Soochow University, Suzhou 215123, People’s Republic of China
4 Suzhou Baolidi Functional Materials Research Institute, Suzhou 215144, People’s Republic of China
Org. Lett.2022, 24, 4620--4624
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.
链接：//pubs.acs.org/doi/10.1021/acs.orglett.2c01736
