Abstract

AbstractThe 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)

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