Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis

Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary one s as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under the present reaction conditions. This method is h ighly practical since operation Is quite simple. Esters and solvents can be used without purification and no inert atmosphere is necessary. The produc ts can be isolated simply by column chromatography or distillation without aqueous workup. (C) 1999 Elsevier Science Ltd. All rights reserved.