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

Abstract

An efficient and highly regioselective method for the synthesis of 3-indolyl-<i>C</i>-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-<i>C</i>-glycosides in 64-87% yields.