title: Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl β-O-glycosides.
abstract: Arylation of 6-O-tert-butyldiphenylsilyl-3,4-di-O-isobutyloxycarbonyl-d-glucal (3) with various phenols in the presence of a catalytic amount of palladium(0) gave the corresponding 2,3- and 3,4-unsaturated β-O-glycosides. The reaction is stereospecific, in all cases, only the β-anomer is formed.
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Kubiak
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors.forename: Robert
authors.initials: R
authors.lastname: Kołodziuk
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors.forename: Stanisław
authors.initials: S
authors.lastname: Porwański
authors.affiliation: Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland. Electronic address: azawisza@chemia.uni.lodz.pl.
authors.forename: Anna
authors.initials: A
authors.lastname: Zawisza
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003847:Deoxyglucose / Q000031:analogs & derivatives*; D006027:Glycosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D010636:Phenols; D010165:Palladium; D003847:Deoxyglucose
keywords: Allylic alkylation reaction; Ferrier rearrangement; Homogeneous catalysis; O-Glycosides; Palladium; d-Glucal