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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Catalytic Site-Selective Acylation of Carbohydrates Directed by Cation-n Interaction.
Journal of the American Chemical Society 2017 March 30
Site-selective functionalization of hydroxyl groups in carbohydrates is one of the long-standing challenges in chemistry. Using a pair of chiral catalysts, we now can differentiate the most prevalent trans-1,2-diols in pyranoses systematically and predictably. Density functional theory (DFT) calculations indicate that the key determining factor for the selectivity is the presence or absence of a cation-n interaction between the cation in the acylated catalyst and an appropriate lone pair in the substrate. DFT calculations also provided a predictive model for site-selectivity and this model is validated by various substrates.
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