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

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Abstract

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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Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies

D. Lee, C. L. Williamson, L. Chan, M. S. Taylor, J. Am. Chem. Soc., 2012, 134, 8260-8267.

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Key Words

benzoates

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ID: J48-Y2011-0630