Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner−Emmons Reagents, Ethyl (Diarylphosphono)acetates
- 1 April 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (7), 1934-1939
- https://doi.org/10.1021/jo970057c
Abstract
New Horner−Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl5, 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.Keywords
This publication has 10 references indexed in Scilit:
- Practical synthesis of Z-unsaturated esters by using a new Horner-Emmons reagent, ethyl diphenylphosphonoacetateTetrahedron Letters, 1995
- A novel 1,8-photoaddition of dimethyl 1,4-naphthalenedicarboxylate to alkenesJournal of the American Chemical Society, 1992
- 1,3-dimethyl 2-oxo 1,3,2-diazaphospholidine precursor of (Z) α,β-unsaturated esters.Tetrahedron Letters, 1991
- Palladium(0)-catalyzed reaction of (Z)-2-butene-1,4-diyl bis(methyl carbonate) and (Z)-2-butene-1,4-diyl diacetate with bifunctional nitrogen nucleophilesThe Journal of Organic Chemistry, 1990
- Modified Wittig Reactions Using Triethylamine and Lithium Halides: Synthesis of ?,?-Unsaturated Esters from Ketones and Ethyl Bis(Trifluoroethyl)PhosphonoacetateSynthetic Communications, 1990
- A triply convergent enantioselective total synthesis of (+)-ikarugamycinJournal of the American Chemical Society, 1989
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsChemical Reviews, 1989
- Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination.Tetrahedron Letters, 1983
- Further synthetic studies on rifamycin sTetrahedron, 1981
- The Stereochemistry of the Phosphonate Modification of the Wittig ReactionThe Journal of Organic Chemistry, 1965