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).
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Description/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.
| Item Type: | Article |
|---|---|
| ISSNs: | 0022-3263 (print) |
| Related URLs: | |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 37582 |
| Date Deposited: | 24 May 2006 |
| Last Modified: | 01 Jun 2011 11:35 |
| Contributors: | Crosignani, Stefano (Author) White, Peter D. (Author) Linclau, Bruno (Author) |
| Date: | 3 September 2004 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/37582 |
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