Stereoselective Synthesis of 2-Deoxy-β-glycosides Using Anomeric O-Alkylation/Arylation
Morris, William J.
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CitationMorris, William J., and Matthew D. Shair. 2009. Stereoselective synthesis of 2-deoxy-β-glycosides using anomeric o-alkylation/arylation. Organic Letters 11(1): 9–12.
AbstractAnomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-β-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-β-glycosides in high yield and high selectivity. The high β-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control.
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