Recognition and Site-Selective Transformation of Monosaccharides by Using Copper(II) Catalysis

We demonstrate copper(II)‐catalyzed acylation and tosylation of monosaccharides. Various carbohydrate derivatives, including glucopyranosides and ribofuranosides, are obtained in high yields and regioselectivities. Using this versatile strategy, the site of acylation can be switched by choice of lig...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-04, Vol.20 (17), p.5013-5018
Main Authors: Chen, I-Hon, Kou, Kevin G. M., Le, Diane N., Rathbun, Colin M., Dong, Vy M.
Format: Article
Language:English
Subjects:
Acylation
Carbohydrates
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Catalysis
Chemistry
Chlorides
Coordination compounds
Copper
Copper - chemistry
Derivatives
Ligands
molecular recognition
Monosaccharides
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
site-selective functionalization
Stereoisomerism
transition metals
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Summary:We demonstrate copper(II)‐catalyzed acylation and tosylation of monosaccharides. Various carbohydrate derivatives, including glucopyranosides and ribofuranosides, are obtained in high yields and regioselectivities. Using this versatile strategy, the site of acylation can be switched by choice of ligand. Preliminary mechanistic studies support nucleophilic addition of a copper–sugar complex to the acyl chloride to be turnover limiting. Sweet solutions: Copper complexes exhibit specific binding affinity to carbohydrates. Utilizing these unique ligand–metal–carbohydrate interactions allows catalytic, site‐selective functionalization of sugars with wide scope. Enabled by the tunability of the metal–ligand complex, switching regioselectivity is facilitated by the appropriate ligand choice (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201400133