Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner−Emmons Reagents, Ethyl (Diarylphosphono)acetates
The Journal of Organic Chemistry1997Vol. 62(7), pp. 1934–1939
Citations Over TimeTop 10% of 1997 papers
Abstract
New Horner-Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl(5), and 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)phosphono]-, and [bis(o-isopropylphenyl)phosphono]acetates (1k-m) were found to be the most effective, giving Z-unsaturated esters with 93-99% selectivity.
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