Palladium(II) acetate catalyzed stereoselective C-glycosidation of peracetylated glycals with arylboronic acids

Authors
Ramnauth, J Poulin, O Rakhit, S Maddaford, SP
Citation
J. Ramnauth et al., Palladium(II) acetate catalyzed stereoselective C-glycosidation of peracetylated glycals with arylboronic acids, ORG LETT, 3(13), 2001, pp. 2013-2015
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
13
Year of publication
2001
Pages
2013 - 2015
Database
ISI
SICI code
1523-7060(20010628)3:13<2013:PACSCO>2.0.ZU;2-7
Abstract
[GRAPHICS] Addition of a variety of arylboronic acids to peracetylated glycals takes p lace in the presence of a catalytic amount of Pd(OAc)(2). The reaction invo lves the syn addition of a sigma -aryl-Pd complex to the glycal double band followed by anti elimination of Pd(OAc)(2) to provide a carbon-ferrier typ e product, This method provides a practical and convenient stereoselective synthesis of C-arylglycosides.