SHORTPAPER	Synthesis 2005: 3193-3195   DOI: 10.1055/s-2005-918452
© Georg Thieme Verlag Stuttgart · New York
Tandem Horner-Wadsworth-Emmons Olefination/Claisen Rearrangement/Hydrolysis Sequence: Remarkable Acceleration in Water with Microwave Irradiation
Ernesto Quesada*,1, Richard J. K. Taylor*
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
Received 21 February 2005

Abstract

A tandem three-step, one-pot method for the conversion of aldehydes into β-substituted-2-oxohex-5-enoic acids 1 in good to excellent yield is described. The optimised sequence is carried out in water with microwave irradiation and involves sequential Horner-Wadsworth-Emmons (HWE) olefination, Claisen rearrangement and ester hydrolysis. The outcome of this domino sequence can be controlled by the temperature of the process.

Key words

tandem reactions - rearrangements - domino reactions - Wittig reactions - carboxylic acids