60415-92-1Relevant academic research and scientific papers
Synthesis of Substituted Furans by Palladium-Catalyzed Cyclization of Acetylenic Ketones
Fukuda, Yukitoshi,Shiragami, Hiroshi,Utimoto, Kiitiro,Nozaki, Hitosi
, p. 5816 - 5819 (2007/10/02)
Palladium-catalyzed cyclization of β,γ-acetylenic ketones gives furans by intramolecular oxypalladation and subsequent protodemetalation. 3-Allylfurans were exclusively obtained by trapping the intermediate 3-furylpalladium species with allyl halides in t
Chiral 2,2-Disubstituted Cyclohexanones; Annulation via Claisen Rearrangement Products
Grattan, T. J.,Whitehurst, J. S.
, p. 11 - 18 (2007/10/02)
The methyl enol ether of 2-methylcyclohexanone reacts regiospecifically with the optical active forms of but-3-yn-2-ol and but-3-en-2-ol. (R)-But-3-yn-2-ol yields an approximately 4:1 mixture of (R)-2-methyl-2-(R-buta-1,2-dienyl)cyclohexanone and the corresponding SR compound.By contrast the but-3-en-2-ol reaction is ca. 96percent enantioselective; (R)-but-3-en-2-ol gives (R)-2-(trans-but-2-enyl)-2-methylcyclohexanone and (S)-but-3-en-2-ol gives the corresponding (S)-cyclohexanone.These Claisen rearrangement products have been transformed into Robinson-type annulated ketones.Cleavage of some highly hindered esters has been carried out efficiently by sodium methylsulphinyl-methanide in dimethyl sulphoxide.
