Regio- and Stereoselective C -Glycosylation of Indoles Using o -[1-( p -MeO-Phenyl)vinyl]benzoates (PMPVB) as Glycosyl Donors under Brønsted Acid Catalysis.

The alkene-based o -[1-( p -MeO-phenyl)vinyl]benzoates (PMPVB) donors that can be remotely activated under catalytic Brønsted acidic conditions have been utilized to synthesize the C -linked indolyl glycosides in a regio- and stereoselective manner. The highly reactive glycosyl donors allow the usage of the poorly nucleophilic N -Boc and N -acetyl indole derivatives, leading to the indolyl glycosides in excellent yields and stereoselectivities. Also, conditions were developed for recycling the byproduct, which significantly improves the potential of these donors.