Title
An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides
Document Type
Article
Publication Date
2-12-2013
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. © 2013 Elsevier Inc. All rights reserved.
Publication Source (Journal or Book title)
Carbohydrate Research
First Page
42
Last Page
47
Recommended Citation
Spell, M., Wang, X., Wahba, A., Conner, E., & Ragains, J. (2013). An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides. Carbohydrate Research, 369, 42-47. https://doi.org/10.1016/j.carres.2013.01.004