Silver(I)-catalyzed addition of zirconocenes to glycal epoxides. A new synthesis of alpha-C-glycosides.
[reaction: see text] Hydrozirconation of terminal alkynes, followed by AgClO4-catalyzed in situ addition of the resultant alkenylzirconocenes to 1,2-anhydrosugars (glycal epoxides) leads to alpha-C-glycosides in moderate to high yields.
Wipf
Peter
P
Department of Chemistry and Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA. pwipf@pitt.edu
Pierce
Joshua G
JG
Zhuang
Nian
N
D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D004852:Epoxy Compounds; D006027:Glycosides; D007202:Indicators and Reagents; D009942:Organometallic Compounds; C023398:Zirconocene dichloride; D012834:Silver; D015040:Zirconium