Both (R) and (S)-2,3-dibromo-l-propanol with e.e. up to 60% 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.
DIASTEREOSELECTIVE BROMINATION OF ALLYL GLYCOSIDES USING TETRABUTYLAMMONIUM TRIBROMIDE
CHIAPPE, CINZIA;D'ANDREA, FELICIA
1995-01-01
Abstract
Both (R) and (S)-2,3-dibromo-l-propanol with e.e. up to 60% 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.File in questo prodotto:
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