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

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