title: Regenerative glycosylation under nucleophilic catalysis.
abstract: This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its consumption until glycosyl acceptor has reacted.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Swati S
authors.initials: SS
authors.lastname: Nigudkar
authors.forename: Keith J
authors.initials: KJ
authors.lastname: Stine
authors.forename: Alexei V
authors.initials: AV
authors.lastname: Demchenko
mesh_terms: D002384:Catalysis; D006031:Glycosylation; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D000078183:Oxindoles; D010100:Oxygen / Q000737:chemistry
chemical_list: C000591251:3,3-difluoroxindole; D007211:Indoles; D000078183:Oxindoles; D010100:Oxygen