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7924746 
Journal Article 
Phosphonate modification for a highly (Z)-selective synthesis of unsaturated esters by Horner-Wadsworth-Emmons olefination 
Touchard, FP 
2005 
Yes 
European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690 
2005 
9 
1790-1794 
English 
WOS:000228959500011 
The Horner-Wadsworth-Emmons (HWE) reaction of various ethyl diarylphosphonoacetates with benzaldehyde, cyclohexane carboxaldehyde and octanal is reported. Selectivities of up to 98% at -78°C are obtained with the three substrates. Among all the phosphonates prepared, the reagent based on 2-tert-butylphenol proved to be especially efficient, with Z/E ratios close to 95:5 at 0°C. It appears thus to be the reagent of choice for the (Z)-selective HWE reaction with both aromatic and aliphatic aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005. 
alkenes; olefination; wittig reaction