Lewis acid-catalyzed cleavage of carbamate and carbonate resins

A procedure for the preparation of amides and esters on a Merrifield resin- bound benzyloxycarbonyl equivalent has been developed. Polymer-supported ca rbamates react cleanly with zinc bromide and the appropriate acyl halide in the presence of triethylamine to provide their corresponding amides in hig h yields and purities. Cleavage of resin-bound carbonates was carried out u sing the similar reagent systems in the absence of triethylamine to give ac etates or benzoates. (C) 2000 Elsevier Science Ltd. All rights reserved.