Recent Advances in Organocatalytic Glycosylations

Carbohydrates play a pivotal role in biological systems and present an opportunity to develop potent carbohydrate-derived therapeutics and diagnostic tools for the treatment and detection of disease. To better comprehend the biological functions of carbohydrates, access to pure and structurally defined oligosaccharides is needed. Oligosaccharides are commonly synthesized by chemical means; however, despite progress in glycosylation chemistry, the efficient and stereoselective formation of glycosidic bonds by mild, nontoxic and low-cost methods remains a challenge. Organocatalysis is an exciting field that utilizes small organic molecules to effect chemical transformation where traditionally transition metal catalysis would be required. This microreview presents recent advances in the application of organocatalysis to carbohydrate chemistry and in particular to the stereoselective synthesis of oligosaccharides.