Regio- and Stereoselective <i>C</i>-Glycosylation of Indoles Using <i>o</i>-[1-(<i>p</i>-MeO-Phenyl)vinyl]benzoates (PMPVB) as Glycosyl Donors under Brønsted Acid Catalysis
Suvendu Halder, Rupa Bai Addanki, Pavan K. Kancharla
Abstract
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.
Topics & Concepts
BenzoatesStereoselectivityGlycosylChemistryIndole testCatalysisAlkeneGlycosylationNucleophileBrønsted–Lowry acid–base theoryGlycosideOrganic chemistryMedicinal chemistryStereochemistryBiochemistryCarbohydrate Chemistry and SynthesisSynthesis of Indole DerivativesSynthesis and Catalytic Reactions