77588-52-4Relevant academic research and scientific papers
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 (1994)
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.
N-Methoxy-N-methyl-3-bromopropionamide: A new three carbon homologating agent for the synthesis of unsymmetrical 1,4-diketones
Selvamurugan,Aidhen
, p. 6065 - 6069 (2007/10/03)
A synthetic route based on a three carbon homologation of an α-aminonitrile was developed for the synthesis of unsymmetrical 1,4-diketones. The key steps were the alkylation of various aryl and heteroaryl α-aminonitriles with N-methoxy-N-methyl-3-bromopropionamide followed by the addition of a Grignard reagent to the alkylated product and then subsequent hydrolysis.
From allylic alcohols to saturated carbonyls using Fe(CO)5 as catalyst: Scope and limitation studies and preparation of two perfume components
Cherkaoui, Hassan,Soufiaoui, Mohammed,Grée, René
, p. 2379 - 2383 (2007/10/03)
The direct conversion of allylic alcohols to saturated carbonyls, using Fe(CO)5 as a catalyst, offers good synthetic potential. Mono-, di- and even trisubstituted alkenes bearing various alkyl, aryl and electronwithdrawing groups on the allylic system give good to excellent yields of rearranged products. Limitations occur mainly with polyunsaturated derivatives. This reaction was applied to a short and efficient synthesis of cyclamen aldehyde and foliaver.
Addition of Aldehydes to Activated Double Bonds, XXV. Syntheses and Reactions of Branched Tricarbonyl Compounds
Stetter, Hermann,Jonas, Friedrich
, p. 564 - 580 (2007/10/02)
Thiazolium salt-catalyzed addition of aldehydes to arylidene- and alkylidene-β-dicarbonyl compounds as well as to 3-acylacrylic esters leads to branched tricarbonyl compounds (1 - 26), which are useful reagents for the synthesis of heterocyclic compounds.
