title: Ligand-Controlled Monoselective C-Aryl Glycoside Synthesis via Palladium-Catalyzed C-H Functionalization of N-Quinolyl Benzamides with 1-Iodoglycals.
abstract: A monoselective synthesis of aryl-C-Δ(1,2)-glycosides from 1-iodoglycals via palladium-catalyzed ortho-C-H activation of N-quinolyl benzamides has been developed. An amino acid derivative was used as a crucial ligand to improve the yield and monoselectivity of the coupling reaction. The utility of this protocol was demonstrated by a concise synthesis of key moieties of some natural products.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Minglong
authors.initials: M
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Youhong
authors.initials: Y
authors.lastname: Niu
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Yan-Fen
authors.initials: YF
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Xin-Shan
authors.initials: XS
authors.lastname: Ye
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D006860:Hydrogen Bonding; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D001549:Benzamides; D006027:Glycosides; D006847:Hydrocarbons, Iodinated; D008024:Ligands; D010165:Palladium