135468-14-3Relevant academic research and scientific papers
Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers
Caravana, Aidan C.,Nagasing, Benjamin,Dhanju, Sandeep,Reynolds, Rebekah G.,Weiss, Emily A.,Thomson, Regan J.
supporting information, p. 6600 - 6611 (2021/05/29)
Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers. Cyclic voltammetry is used to gain insight into the oxidation events of the reaction.
Synthesis of α,ω-Bis-Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides
Wiesler, Stefan,Bau, Michael A.,Niepel, Thomas,Younas, Sara L.,Luu, Hieu-Trinh,Streuff, Jan
, p. 6246 - 6260 (2019/09/10)
An efficient double addition of substituted alkenylmagnesium bromides to bis-Weinreb amides has been developed, giving α,ω-bis-enones that are building blocks for certain drugs and polymers. Furthermore, reliable protocols for the preparation of the requi
Synthesis of functionalized tetrahydrofuran derivatives from 2,5-dimethylfuran through cascade reactions
Li,Muller,Pera-Titus,Jér?me,De Oliveira Vigier
, p. 2601 - 2609 (2019/06/03)
A three-step strategy is proposed for the functionalization of the methyl group of 2,5-dimethylfuran, encompassing the ring opening of 2,5-dimethylfuran to 2,5-hexanedione, its further aldol condensation with aldehydes, and hydrogenation-cyclization of the condensation intermediate to generate alkylated tetrahydrofuran. Active and selective catalysts could be identified for the aldol condensation and hydrogenation-cyclization reactions.
DICARBONYL DERIVATIVES AND METHODS OF USE
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Page/Page column 36, (2008/12/05)
Derivatives of dicarbonyl compounds having antitumor and antibiotic activity which can be used as anticancer agents.
Palladium-Catalyzed Reductive Coupling of Acid Chlorides with β-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects
Echavarren, Antonio M.,Perez, Marta,Castano, Ana M.,Cuerva, Juan M.
, p. 4179 - 4185 (2007/10/02)
The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate.The double bond conjugated with a single carbonyl group was not significantly reduced.The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine.By performing the reaction at lower temperatures, α,β-unsaturated 1,4-diketones can also be prepared.The reduction of the intermediate α,β-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu3SnCl, followed by hydrolysis of the intermediate palladium enolate.
Facile Synthesis of 1,4-Diketones via Palladium Complex Catalyzed Isomerization of Alkynediols
Lu, Xiyan,Ji, Jianguo,Ma, Dawei,Shen, Wei
, p. 5774 - 5778 (2007/10/02)
Alkynediols isomerized under the catalysis of Pd(dba)3*CHCl3 + 2n-Bu3P in acetonitrile at 80 deg C to give 1,4-diketones in high yields.This experimentally simple and economically synthetic method is illustrated with examples including substituents such as alkyl, alkenyl, and aryl groups.The order of reactivity of the substituents in this reaction is aryl >/= alkenyl > alkyl.Alkenyl-substituted alkynediols chemoselectively isomerized to the corresponding α,β-unsaturated 1,4-diketones.The usefulness of this novel method is examplified by the synthesis of dihydrojasmone.
