A. Kirschning et al., Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals, TETRAHEDR L, 40(51), 1999, pp. 8999-9002
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.