75359-70-5Relevant academic research and scientific papers
Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides
dos Passos Gomes, Gabriel,Yaremenko, Ivan A.,Radulov, Peter S.,Novikov, Roman A.,Chernyshev, Vladimir V.,Korlyukov, Alexander A.,Nikishin, Gennady I.,Alabugin, Igor V.,Terent'ev, Alexander O.
supporting information, p. 4955 - 4959 (2017/04/24)
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from 1,5-dicarbonyl compounds and H2O2. The tetraoxane products generally formed in reaction
Route to Highly Substituted Pyridines
Hilf, Justin A.,Holzwarth, Michael S.,Rychnovsky, Scott D.
, p. 10376 - 10382 (2016/11/17)
Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Hosomi-Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.
Synergistic Cu-amine catalysis for the enantioselective synthesis of chiral cyclohexenones
Quintard,Rodriguez
supporting information, p. 9523 - 9526 (2015/06/08)
An unprecedented utilization of 1,3-acetonedicarboxylic acid as a 1,3-bis-pro-nucleophile and a reactive acetone surrogate in enantioselective catalysis has been reported. By synergistically activating the ketodiacid by copper catalysis and an α,β-unsatur
Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
Molander, Gary A.,Camera, Kimberly O.
, p. 830 - 846 (2007/10/02)
Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.
Observations sur l'hydrolyse d'acetals dihydropyranniques
Thuy, Vu Moc,Maitte, Pierre
, p. 497 - 499 (2007/10/02)
The hydrolysis of of dihydropyranyl acetals by sulfuric acid leads to cyclenones, but by the use of pyridinium p-tolenesulfonate, δ-ketoaldehydes may be isolated.These compounds do not undergo aldol condensation under these conditions.
LATENT ACETONYLATION OF α,β-ENONES WITH ALLYLTRIMETHYLSILANE OR 2-METHYL-2-PROPENYLTRIMETHYLSILANE: SYNTHESIS OF 1,5-DIKETONES AND ANNELATION TO FUSED CYCLOHEXENONES
Hosomi, Akira,Kobayashi, Hiroshi,Sakurai, Hideki
, p. 955 - 958 (2007/10/02)
Acetonylation of α,β-enones can be achieved by either with (2-methyl-2-propenyl)trimethylsilane or with allyltrimethylsilane followed by oxidative cleavage of the double bond or by the Wacker reaction, respectively.Annelation of the 1,5-diketones is also
