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Synthesis of Cyclopenta[b]indoles via Sc(III)-Catalyzed Annulation of Vinyl Diazoacetates with Indole-Derived Unsaturated Imines.

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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… Click to show full 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.

Keywords: catalyzed annulation; annulation; vinyl diazoacetates; synthesis cyclopenta; unsaturated imines

Journal Title: Organic letters
Year Published: 2023

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