1817-27-2Relevant academic research and scientific papers
New Functionalized Horner-Wadsworth-Emmons Reagents: Useful Building Blocks in the Synthesis of Polyunsaturated Aldehydes. A Short Synthesis of (+/-)-(E,E)-Coriolic Acid
Kann, Nina,Rein, Tobias,Akermark, Bjoern,Helquist, Paul
, p. 5312 - 5323 (2007/10/02)
The new Horner-Wadsworth-Emmons reagents 4 and 5 transform carbonyl compounds into 2,4-pentadienals and 3-methyl-2,4-pentadienals, respectively.Reagent 4 gives good yields of the desired products with a variety of aldehydes and ketones; reagent 5 generally gives good yields with aldehydes, but gives lower yields with ketones.The reactions proceed under mild conditions and give the products as predominantly 2E,4E isomers, with moderate to good stereoselectivity.In general, pure samples of the 2E,4E-dienals can be obtained after chromatography.Reagents 4 have been used in the key step in a short synthesis of (+/-)-13-hydroxy-9(E),11(E)-octadecanoic acid ((E,E)-coriolic aicd, 45).
ORGANOLITHIENS VINYLIQUES A FONCTION CARBONYLEE MASQUEE EQUIVALENTS SYNTHETIQUES D'ANIONS EN ω DU METHYL-3 SORBALDEHYDE
Duhamel, Lucette,Duhamel, Pierre,Lecouve, Jean-Pierre
, p. 4349 - 4358 (2007/10/02)
Functionalized organovinylic compounds 1 are prepared by bromine-lithium exchange in ether at -70 deg C.Their condensation with aldehydes and ketones leads to polyenals, directly in the case of 1c and 1d, in two steps in the case of 1a and 1b.Dehydrocitra
