title: Recognition and site-selective transformation of monosaccharides by using copper(II) catalysis.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA).
authors.forename: I-Hon
authors.initials: IH
authors.lastname: Chen
authors.forename: Kevin G M
authors.initials: KG
authors.lastname: Kou
authors.forename: Diane N
authors.initials: DN
authors.lastname: Le
authors.forename: Colin M
authors.initials: CM
authors.lastname: Rathbun
authors.forename: Vy M
authors.initials: VM
authors.lastname: Dong
mesh_terms: D000215:Acylation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D009005:Monosaccharides; D003300:Copper
keywords: carbohydrates; catalysis; molecular recognition; site-selective functionalization; transition metals