ArticleJournal of the American Chemical Society2026
Catalyst-Controlled Chemoselective β-Mannosylation of Phenols Via Attractive Noncovalent Interactions.
Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
We report the development of chemo- and stereoselective phenolic β-mannosylations catalyzed by precisely tuned bis-thiourea H-bond donors. β-Mannosylation of phenols is demonstrated to occur selectively in the presence of primary and secondary alcohols as well as thiols and thiophenols. Kinetic and computational studies support a mechanism of nucleophile activation promoted by general base-catalysis and enhanced by aromatic interactions between the catalyst and the phenolic substrate. The reactions obey Michaelis-Menten kinetics, and selectivity for glycosylation of phenols over aliphatic alcohols can be ascribed to a combination of stronger binding of the nucleophile to the catalyst and higher reaction rate of the bound complex. In contrast, selectivity of phenols over more acidic thiophenols is achieved exclusively through preferential binding to the catalyst.
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