title: Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates.
abstract: Gold(III) bromide is a suitable catalyst for the stereoselective cyclization of 2-C-malonyl carbohydrates to the anomeric center under retention of one ester group. Reopening of the lactones with alcohols in the presence of TMSOTf affords allyl, propargyl and benzyl glycosides with high α-selectivity.
authors.affiliation: Department of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany.
authors.forename: Tukaram M
authors.initials: TM
authors.lastname: Pimpalpalle
authors.forename: Srinivasa Rao
authors.initials: SR
authors.lastname: Vidadala
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
authors.forename: Torsten
authors.initials: T
authors.lastname: Linker
mesh_terms: D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000737:chemistry*; D006046:Gold / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000438:Alcohols; D006027:Glycosides; D007783:Lactones; D058116:Lewis Acids; D006046:Gold