Diastereoselective Bromination of Allyl Glycosides Using Tetrabutylammonium Tribromide

Article abstract of DOI:10.1016/0957-4166(94)00378-O

Both (R) and (S)-2,3-dibromo-1-propanol with e.e. up to 60percent have been obtained by diastereoselective addition of Br2 to allyl glucosides and galactosides having only one unprotected hydroxyl group at C-2 or C-6 using tetrabutylammonium tribromide, followed by hydrolysis.The absolute configuration is shown to depend on the position of the free hydroxyl and on the configuration at the anomeric centre.