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

The alkene-based o-[1-(p-MeO-phenyl)vinyl]benzoates (PMPVB) donors that can be remotely activated under catalytic Bronsted 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.

Automated summary

The alkene-based o-[1-(p-MeO-phenyl)vinyl]benzoates (PMPVB) donors have been successfully used for the regio- and stereoselective synthesis of C-linked indolyl glycosides under catalytic Bronsted acidic conditions. The highly reactive glycosyl donors enable the use of poorly nucleophilic N-Boc and N-acetyl indole derivatives, resulting in excellent yields and stereoselectivities of the indolyl glycosides. Furthermore, conditions for recycling the byproduct have been developed, significantly improving the potential of these donors.