Synthesis of Cyclopenta[<i>b</i>]indoles via Sc(III)-Catalyzed Annulation of Vinyl Diazoacetates with Indole-Derived Unsaturated Imines
Qin Jiang, Ting Yang, Qi Li, Guang‐Ming Liang, Yong Liu, Cheng‐Yu He, Wen‐Dao Chu, Quan‐Zhong Liu
Abstract
A Lewis acid Sc(OTf) 3 -catalyzed annulation reaction of vinyl diazoacetates with in situ formed α,β-unsaturated imines for the preparation of indole-fused tricyclic rings has been reported. This strategy involves a sequential addition/rebound addition process of vinyl diazoacetates and an in situ dedinitrogenation. This annulation protocol features low-cost catalysts, mild reaction conditions, and facilely prepared substrates.
Topics & Concepts
AnnulationIndole testChemistryCatalysisLewis acids and basesTricyclicCombinatorial chemistryMedicinal chemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis