title: An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides.
abstract: Exceptionally mild procedures for the visible light photocatalytic activation of selenoglycoside donors in the presence of alcohol acceptors have been developed. This process is demonstrated with both 1-phenylselenyl-2,3,4,6-tetra-O-benzyl glucoside (1) and 1-phenylselenyl-2,3,4,6-tetra-O-benzyl galactoside (2). Catalysis is effected with both metal (Ru(bpy)3) and organocatalysts (diphenyldiselenide). Reactions afford, in all cases, primarily the α-anomers with selectivities that vary with solvent. This represents the first example of a visible light-promoted O-glycosylation.
authors: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA 70803, United States.
authors: Mark
authors: M
authors: Spell
authors: Xiaoping
authors: X
authors: Wang
authors: Amir E
authors: AE
authors: Wahba
authors: Elizabeth
authors: E
authors: Conner
authors: Justin
authors: J
authors: Ragains
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D008027:Light; D010777:Photochemistry / Q000379:methods*
chemical_list: D000438:Alcohols; D006027:Glycosides