Borinic Acid-Catalyzed Regioselective Acylation of Carbohydrate Derivatives
Doris Lee and Mark S. Taylor*
*Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada, Email: mtaylorchem.utoronto.ca
D. Lee, M. S. Taylor, J. Am. Chem. Soc., 2011, 133, 3724-3727.
DOI: 10.1021/ja110332r (free Supporting Information)
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Reversible covalent interactions of organoboron compounds enable a regioselective borinic acid-catalyzed acylation of polyols. This catalytic protocol enables differentiation of the secondary OH groups of a wide range of carbohydrate derivatives with diverse acid chloride and chloroformate reagents, using a structurally simple diarylborinic acid-derived catalyst.
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D. Lee, C. L. Williamson, L. Chan, M. S. Taylor, J. Am. Chem. Soc., 2012, 134, 8260-8267.