DIASTEREOSELECTIVE BROMINATION OF ALLYL GLYCOSIDES USING TETRABUTYLAMMONIUM TRIBROMIDE

Authors
BELLUCCI G CHIAPPE C DANDREA F
Citation
G. Bellucci et al., DIASTEREOSELECTIVE BROMINATION OF ALLYL GLYCOSIDES USING TETRABUTYLAMMONIUM TRIBROMIDE, Tetrahedron : asymmetry, 6(1), 1995, pp. 221-230
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
1
Year of publication
1995
Pages
221 - 230
Database
ISI
SICI code
0957-4166(1995)6:1<221:DBOAGU>2.0.ZU;2-Z
Abstract
Both (R) and (S)-2,3-dibromo-1-propanol with e.e. up to 60% have been obtained by diastereoselective addition of Bq to allyl glucosides and galactosides having only one unprotected hydroxyl group at C-2 or Cd u sing tetrabutylammonium tribromide, followed by hydrolysis. The absolu te configuration is shown to depend on the position of the free hydrox yl and on the configuration at the anomeric centre.