Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals

Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on t he hypervalent reagent initially employed for oxidizing polymer-bound halid es 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out . With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides a re generated in excellent yield. Free hydroxy groups are tolerated. Even, f ully unprotected glucal 23 can be employed for the short synthesis of 2-deo xy-2-iodo glycosyl acetates 24a,b. (C) 1999 Elsevier Science Ltd. All right s reserved.