Litcius/Paper detail

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

Wenbin Cao, Jiandong Zhang, Mengmeng Xu, Huawei Liu, Haiyan Li, Xiaoping Xu, Shun‐Jun Ji

2022Organic Letters18 citationsDOI

Abstract

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.

Topics & Concepts

ChemistryStereoselectivityAminationIndole testCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsChemical Synthesis and Analysis
<i>Syn</i>-Stereoselective C3-Spirocyclization and C2-Amination of 3-(2-Isocyanoethyl)indole Using <i>C</i>,<i>N</i>-Cyclic Azomethine Imines | Litcius