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Synthetic communications, v.31 no.1, 2001년, pp.89 - 95
Petroski, Richard (National Center for Agricultural Utilization Research, 1USDA, REE, Agricultural Research Service, Bioactive Agents Research Unit and Analytical Support Unit, 1815 N. University Street, Peoria, IL, 61604, U.S.A.) , Weisleder, David (National Center for Agricultural Utilization Research, 1USDA, REE, Agricultural Research Service, Bioactive Agents Research Unit and Analytical Support Unit, 1815 N. University Street, Peoria, IL, 61604, U.S.A.)
The E -isomer selectivity of the Horner-Wadsworth-Emmons olefination of aldehydes to form a-methyl- or a-ethyl-a,ß-unsaturated esters has been improved by using lithium tert -butoxide as the base, triethyl-2-phosphonopropionate or triethyl-2-phospho-nobutyrate as the phosphonate, an aldehyde, and hexane as the reaction solvent. Greater E -isomer selectivity was observed in the formation of a-methyl-a,ß-unsaturated esters than a-ethyl-a,ß-unsaturated esters. These compounds are useful intermediates for the synthesis of insect pheromones and natural products.
Recent Res. Devel. in Entomol. Bartelt R. J. 115 1997
Bartelt, Robert J., Weisleder, David, Plattner, Ronald D.. Synthesis of nitidulid beetle pheromones: alkyl-branched tetraene hydrocarbons. Journal of agricultural and food chemistry, vol.38, no.12, 2192-2196.
Johnson, W. A. 1993. Ylides and Imines of Phosphorous 326New York: John Wiley & Sons, Inc.
10.1055/s-1985-31438
Alvarez-Ibarra, Carlos, Arias, Selma, Bañón, Gabriel, Fernández, María J., Rodríguez, Miguel, Sinisterra, Vicente. An efficient and stereoselective Wittig–Horner synthesis of acyclic α-enones with barium hydroxide as solid catalyst. Journal of the Chemical Society, Chemical communications, vol.1987, no.19, 1509-1511.
Bonadies, F., Cardilli, A., Lattanzi, A., Orelli, L.R., Scettri, A.. A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.35, no.20, 3383-3386.
Brouwer, H., Stothers, J. B.. 13 C Nuclear Magnetic Resonance Studies. XVI. 13 C Spectra of some Substituted Acrylic Acids and their Methyl Esters. A Correlation of Olefinic Shieldings in α,β-unsaturated Carbonyl Systems. Canadian journal of chemistry, vol.50, no.5, 601-611.
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