title: Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway.
abstract: An efficient and concise method for the construction of various O-glycosidic bonds by a palladium-catalyzed reaction with a 3-O-picoloyl glucal has been developed. The stereochemistry of the anomeric center derives from either an inner-sphere or outer-sphere pathway. Harder nucleophiles, such as aliphatic alcohols and sodium phenoxides give β-products, and α products result from using softer nucleophiles, such as phenol.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Shaohua
authors.initials: S
authors.lastname: Xiang
authors.forename: Kim Le Mai
authors.initials: Kle M
authors.lastname: Hoang
authors.forename: Jingxi
authors.initials: J
authors.lastname: He
authors.forename: Yu Jia
authors.initials: YJ
authors.lastname: Tan
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D002384:Catalysis; D006031:Glycosylation; D010165:Palladium / Q000737:chemistry*
chemical_list: D010165:Palladium
keywords: alcohols; glycosylation; nucleophilicity; palladium; reaction mechanism