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

The Journal of Organic Chemistry
Stefano CrosignaniBruno Linclau

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.

References

Jan 5, 1999·Bioorganic & Medicinal Chemistry Letters·J S WarmusK D Brady
Jun 12, 2003·Angewandte Chemie·R Ian StorerSteven V Ley
Aug 30, 2003·Organic & Biomolecular Chemistry·Rachel N MacCossSteven V Ley
Feb 12, 2004·Molecular Diversity·Stefano CrosignaniMark Bradley

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Citations

Mar 15, 2006·Drug Discovery Today·Farah Mavandadi, Ake Pilotti
Nov 3, 2020·Chemistry : a European Journal·S Maryamdokht TaimooryRyan Guterman
Apr 5, 2018·The Journal of Organic Chemistry·Hikaru FujitaMunetaka Kunishima
Dec 20, 2017·The Journal of Organic Chemistry·Ryan GutermanMarkus Antonietti
Apr 22, 2006·The Journal of Organic Chemistry·Alan R KatritzkySergey Bobrov
Nov 15, 2005·Journal of Combinatorial Chemistry·Roland E Dolle
Oct 19, 2007·Journal of Agricultural and Food Chemistry·Chia-Ying LiLe Thanh

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