Tris(pentafluorophenyl)borane-Catalyzed Stereoselective C-Glycosylation of Indoles with Glycosyl Trichloroacetimidates: Access to 3-Indolyl-C-glycosides

Dubey, Atul; Tiwari, Ashwani; Mandal, Pintu Kumar

Tris(pentafluorophenyl)borane-Catalyzed Stereoselective C-Glycosylation of Indoles with Glycosyl Trichloroacetimidates: Access to 3-Indolyl-C-glycosides

2021

Dubey, Atul | Tiwari, Ashwani | Mandal, Pintu Kumar

An efficient and highly regioselective method for the synthesis of 3-indolyl-C-glycosides has been developed through coupling of glycosyl trichloroacetimidates with a wide range of substituted indoles in the presence of catalytic amounts of B(C₆F₅)₃ within a few minutes. This methodology has a wide scope of substrates under mild reaction conditions and provides exclusively β-stereoselective 3-indolyl-C-glycosides in 64–87% yields.

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