54783-55-0Relevant academic research and scientific papers
Catalytic Conjugate Addition of Electron-Rich Heteroarenes to β,β-Disubstituted Enones
Metz, Tanner L.,Evans, Joshua,Stanley, Levi M.
supporting information, p. 3442 - 3445 (2017/07/15)
Catalytic conjugate additions of heteroarenes to β,β-disubstituted enones are reported. Additions of a range of heteroarene nucleophiles, including furans, indoles, a pyrrole, and a thiophene, to a variety of β,β-disubstituted enones occur to form the corresponding ketone products containing heteroarylated, all-carbon quaternary centers in up to 90% yield. These reactions occur under mild reaction conditions in the presence of low loadings of bismuth triflate.
Niobium pentachloride activation of enone derivatives: Diels-Alder and conjugate addition products
Gomes Constantino, Mauricio,Lacerda Jr., Valdemar,Da Silva, Gil Valdo José
, p. 456 - 464 (2007/10/03)
Niobium pentachloride has proven to be a powerful activating agent for Diels-Alder or conjugate addition reactions of cycloenones. The Diels-Alder product was obtained only with an unsubstituted enone (cyclohexenone) and the highly reactive diene cyclopentadiene; substituents in the β-position of enones seem to prevent Diels-Alder reaction: oxygenated substituents favor the formation of vinyl chlorides (ethyl ether or dichloromethane as solvents) or enol ethers (ethyl acetate as solvent), while a methyl substituent prevents (any kind of transformation with NbCl5. Less reactive dienes, furan and 2-methylfuran gave the conjugate addition products of the furan ring to the enone system.
An easy route to 11-hydroxy-eudesmanolides. Synthesis of (±) decipienin A
Moreno-Dorado, F. Javier,Guerra, Francisco M.,Aladro, F. Javier,Bustamante, Jesus M.,Jorge, Zacarias D.,Massanet, Guillermo M.
, p. 6997 - 7010 (2007/10/03)
The preparation of 11-hydroxy-eudesmanolides with the stereochemistry found in the Umbelliferae family of plants is described. The decalin system of the eudesmane skeleton is produced by the addition of 5-methyl-2- furyllithium to 3-ethoxycyclohex-2-enone and acidic treatment of the resulting adduct. The stereochemistry of the decalones obtained by this method has been corrected. The α-hydroxy-γ-lactone moiety is obtained by condensation of the appropriate decalone with methyl pyruvate and subsequent reduction under Luche conditions. The usefulness of this procedure has been proven in the synthesis of decipienin A.
