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

Polymer-supported O-alkylisoureas: useful reagents for the O-alkylation of carboxylic acids
Polymer-supported O-alkylisoureas: useful reagents for the O-alkylation of carboxylic acids
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.
0022-3263
5897-5905
Crosignani, Stefano
aaa5cc3f-0b82-4d33-af01-59115c8bdff5
White, Peter D.
d33665ca-e96f-4f8b-b016-a9a7e845f7c3
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Crosignani, Stefano
aaa5cc3f-0b82-4d33-af01-59115c8bdff5
White, Peter D.
d33665ca-e96f-4f8b-b016-a9a7e845f7c3
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

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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More information

Published date: 3 September 2004

Identifiers

Local EPrints ID: 37582
URI: https://eprints.soton.ac.uk/id/eprint/37582
ISSN: 0022-3263
PURE UUID: 5ff4c906-fb49-4885-bad0-92effc6e3327
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 24 May 2006
Last modified: 18 Jul 2019 12:28

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