188945-39-3Relevant academic research and scientific papers
Phosphonate modification for a highly (Z)-selective synthesis of unsaturated esters by Horner-Wadsworth-Emmons olefination
Touchard, Francois P.
, p. 1790 - 1794 (2007/10/03)
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.
Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner-Emmons Reagents, Ethyl (Diarylphosphono)acetates
Ando, Kaori
, p. 1934 - 1939 (2007/10/03)
New Horner-Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl5 the corresponding phenols. The reaction of 1 with several kinds of aldehydes in the presence of Triton B or NaH in THF solvent revealed that these reagents are useful for the synthesis of Z-unsaturated esters. Among the reagents examined, ethyl(di-o-tolylphosphono)-, [bis(o-ethylphenyl)phosphonol-, and [bis(o-isopropylphenyl)phosphono]acetates (1k-m) were found to be the most effective, giving Z-unsaturated esters with 93-99% selectivity.
