3214-41-3Relevant academic research and scientific papers
One-pot synthesis of γ-diketones, γ-keto esters, and conjugated cyclopentenones from nitroalkanes
Ballini, Roberto,Barboni, Luciano,Bosica, Giovanna,Fiorini, Dennis
, p. 2725 - 2728 (2002)
Conjugated addition of primary nitroalkanes to α,β-unsaturated ketones or α,β-unsaturated esters, in the presence of two equivalents of DBU, allows the one-pot prepration of γ-diketones or γ-keto esters, respectively. When 2-aryl-1-nitroethane derivatives
Synthesis of 2,5-Disubstituted Pyrrolidine Alkaloids via A One-Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts
Costa, Bruna Z.,Galman, James L.,Slabu, Iustina,France, Scott P.,Marsaioli, Anita J.,Turner, Nicholas J.
, p. 4733 - 4738 (2018/09/25)
A multi-enzymatic cascade process involving transaminases (TAs) and reductive aminases (RedAms) to produce enantiomerically pure 2,5-disubstituted pyrrolidine alkaloids from their respective 1,4-diketones is reported. Several TAs were screened and the best results for diketone monoamination were obtained with an R-selective TA from Mycobacterium chlorophenicum and with an S-selective TA from Bacillus megaterium. Pyrroline reduction was best performed by a reductive aminase from Ajellomyces dermatitidis (AdRedAm). Finally, a biocatalytic one-pot cascade was implemented using the aforementioned enzymes and a variety of 2-methyl-5-alkylpyrrolidines were produced with high (>99 %) conversion, diastereomeric and enantiomeric excess values.
Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Dewez, Damien F.,Du, Le,Luo, Xiya,Markó, István E.,Lam, Kevin
, (2018/10/15)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Du, Le,Luo, Xiya,Markó, István E.,Dewez, Damien F.,Lam, Kevin
, p. 12044 - 12055 (2019/03/01)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
NOVEL PROCESS FOR PREPARING SYNTHESIS INTERMEDIATES USING PRODUCTS OF NATURAL ORIGIN AND USE OF THE INTERMEDIATES OBTAINED
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Paragraph 0231, (2017/12/15)
Disclosed is a process for preparing a product of formula I: wherein the reaction is catalyzed both by thiamine or a thiamine salt and by ascorbic acid in a form which is free or salified or an organic acid salt of an alkaline metal, preferably sodium acetate, potassium tartrate, sodium succinate, or a reductone, preferably 2-hydroxypropanedial or 2,3-dihydroxycyclopent-2-ene-1-one in an organic solvent.
Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation
Pridmore, Simon J.,Slatford, Paul A.,Taylor, James E.,Whittlesey, Michael K.,Williams, Jonathan M.J.
supporting information; experimental part, p. 8981 - 8986 (2009/12/27)
Alkyne-1,4-diols are readily available substrates which are isomerised to 1,4-diketones using Ru(PPh3)3(CO)H2/xantphos as a catalyst. In situ cyclisation into furans, pyrroles and pyridazines has been achieved under suitable conditions.
2,5-Disubstituted furans from 1,4-alkynediols
Pridmore, Simon J.,Slatford, Paul A.,Williams, Jonathan M.J.
, p. 5111 - 5114 (2008/02/09)
1,4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)3(CO)H2 with Xantphos at 1 mol % loading.
Unprecedented, selective Nef reaction of secondary nitroalkanes promoted by DBU under basic homogeneous conditions
Ballini, Roberto,Bosica, Giovanna,Fiorini, Dennis,Petrini, Marino
, p. 5233 - 5235 (2007/10/03)
Secondary nitrocompounds can be converted into the corresponding ketones under basic conditions using DBU in acetonitrile. Primary nitroalkanes are unaffected by these conditions. Elsevier Science Ltd. All rights reserved.
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.
A convenient synthesis of 1,4-diketones
Motoyoshiya,Hongo,Tanaka,Hayashi
, p. 997 - 1000 (2007/10/02)
A simple and short synthesis of 1,4-diketones was achieved via 2-chloro-5-methylthio-2,5-hexadienes and their hydrolysis with titanium tetrachloride.
