Polymer-supported O-alkylisoureas: useful reagents for the O-alkylation of carboxylic acids

Crosignani, Stefano, White, Peter D. and Linclau, Bruno (2004) Polymer-supported O-alkylisoureas: useful reagents for the O-alkylation of carboxylic acids. Journal of Organic Chemistry, 69 (18), 5897-5905. (doi:10.1021/jo049239e).

Record type: Article

Abstract

Polymer-supported O-alkylisoureas were prepared by reaction of an alcohol with a polymer-supported carbodiimide under copper(II) catalysis. These reagents were used to transform carboxylic acids into the corresponding methyl, benzyl, allyl, and p-nitrobenzyl esters in a highly chemoselective manner in high yields and in very high purity after simple resin filtration and solvent evaporation. The reactions could be carried out using both conventional or microwave heating, with reaction times as short as 3-5 min in the latter case, without compromising yield, purity, or chemoselectivity. Unfortunately, the corresponding solid-supported tert-butyl isoureas could not be prepared.

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