Stereoretentive reactions have recently emerged as a powerful strategy to construct glycosidic bonds through metal-catalyzed transformations of anomeric nucleophiles. These two-electron processes allow for a consistently high control of anomeric configuration with a broad range of substrates, including saccharides with free hydroxyl groups. However, single-electron reactions generating anomeric radicals represent an attractive alternative. To harness these intermediates, we recently studied stereoelectronic interactions in complexes of late transition metals located at the C1 position and described a general axial preference termed as the metallo-anomeric effect. In this lecture, I will highlight our latest developments in the area of glycosyl cross-couplings including applications of the metallo-anomeric effect in constructing high-value glycoconjugates. These studies demonstrate an effective combination of experimental and computational techniques in developing new methods for carbohydrate synthesis.

Recent advances in glycosyl cross-coupling reactions

ACS Fall 2021

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