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Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration

Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration
Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration
The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for SN2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using an in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient “catch and release” ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.
0022-3263
4753-4762
Chighine, Alessandra
6d8eb5fe-90c5-44a6-91dc-86d7baad443a
Crosignani, Stefano
aaa5cc3f-0b82-4d33-af01-59115c8bdff5
Arnal, Marie-Claire
545ec18d-6984-4dd7-8bb2-cd167f366edc
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Chighine, Alessandra
6d8eb5fe-90c5-44a6-91dc-86d7baad443a
Crosignani, Stefano
aaa5cc3f-0b82-4d33-af01-59115c8bdff5
Arnal, Marie-Claire
545ec18d-6984-4dd7-8bb2-cd167f366edc
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Chighine, Alessandra, Crosignani, Stefano, Arnal, Marie-Claire, Bradley, Mark and Linclau, Bruno (2009) Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration. Journal of Organic Chemistry, 74 (13), 4753-4762. (doi:10.1021/jo900476y).

Record type: Article

Abstract

The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for SN2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using an in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient “catch and release” ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.

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More information

Published date: 3 July 2009

Identifiers

Local EPrints ID: 147919
URI: https://eprints.soton.ac.uk/id/eprint/147919
ISSN: 0022-3263
PURE UUID: 0eb78a85-4ac1-4d1c-9c66-1c7c8c997aa8
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 27 Apr 2010 13:57
Last modified: 06 Jun 2018 12:52

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