An alpha-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides

作者：Spell Mark; Wang Xiaoping; Wahba Amir E; Conner Elizabeth; Ragains Justin^*

来源：Carbohydrate Research, 2013, 369: 42-47.

DOI：10.1016/j.carres.2013.01.004

• Chemical O-glycosylation
• Photoredox catalysis
• Visible light photocatalysis
• Selenoglycosides

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 alpha-anomers with selectivities that vary with solvent. This represents the first example of a visible light-promoted O-glycosylation.

• 出版日期2013-3-22