Phenolic nucleophiles were also demonstrated to be useful partners in the catalytic couplings, albeit under a slightly modified reaction protocol. Increased dilution relative to the glucosylation of alcohols ([4]0 = 0.025 M vs. [3]0 = 0.2 M), and addition of basic alumina were found to enhance βselectivity (Figures ). Phenols bearing functionality such as amides (4a) and indoles (4b) proved to be effective coupling partners. In addition, tertiary-amine-containing (4c) and sterically hindered (4d) phenols underwent 2-deoxyglucosylation with good levels of β-selectivity, albeit in modest yields. Finally, glucosylation of β-estradiol 4e was observed to occur with moderate selectivity for the phenolic position.