14807-28-4Relevant academic research and scientific papers
A new approach to arylaliphatic 1,5-, 1,6-, and 1,7-dicarbonyl compounds and their monoacetals based on direct anodic oxidation of 1-phenyl- and benzo[c]cycloalkenes
Ogibin,Ilovaisky,Nikishin
, p. 1939 - 1941 (1996)
A new simple approach to ω-benzoylalkanals, 2-(ω-formylalkyl)benzaldehydes, and their monoacetals was developed based on direct anodic oxidation of 1-phenylcycloalkenes and benzo[c]cycloalkenes in methanol followed by acid hydrolysis of the electrolysis p
An Improved Stereocontrolled Access Route to Piperidine or Azepane β-Amino Esters and Azabicyclic β- and γ-Lactams; Synthesis of Novel Functionalized Azaheterocyles
Ouchakour, Lamiaa,Nonn, Melinda,Remete, Attila M.,Kiss, Loránd
, p. 3874 - 3885 (2021/06/16)
An improved, efficient synthesis of some functionalized saturated azaheterocycles has been accomplished by controlled functionalization of various readily available cyclic compounds containing ring C=C bond. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of various unsaturated scaffolds across ozonolysis followed by ring closing with double reductive amination with primary alkylamines or fluorinated alkylamines. The protocol provided versatile azaheterocyclic derivatives with a piperidine or azepane framework.
A de novo synthetic method to the access of N-substituted benzazepines
Ouchakour, Lamiaa,Nonn, Melinda,D'hooghe, Matthias,Kiss, Loránd
, (2020/02/04)
A novel, convenient procedure has been described for the construction of fluorine-containing benzazepines. The synthetic protocol starting from readily available dihydronaphthalene regioisomers is based on oxidative ring olefin bond cleavage followed by r
Regioselective biocatalytic self-sufficient Tishchenko-type reactionviaformal intramolecular hydride transfer
Buljubasic, Isa,Hall, Mélanie,Laggner, Olivia,Merusic, Kemal,Reiter, Tamara,Tassano, Erika,Vogel, Andreas
, p. 6340 - 6343 (2020/06/21)
A self-sufficient nicotinamide-dependent intramolecular bio-Tishchenko-type reaction was developed. The reaction is catalyzed by alcohol dehydrogenases and proceeds through formal intramolecular hydride transfer on dialdehydes to deliver lactones. Regioselectivity on [1,1′-biphenyl]-2,2′-dicarbaldehyde substrates could be controlledviathe electronic properties of the substituents. Preparative scale synthesis provided access to substituted dibenzo[c,e]oxepin-5(7H)-ones.
Rate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes: A remarkable 2-substituent effect
Collett, Christopher J.,Massey, Richard S.,Taylor, James E.,Maguire, Oliver R.,O'Donoghue, AnnMarie C.,Smith, Andrew D.
supporting information, p. 6887 - 6892 (2015/06/02)
Abstract Rate and equilibrium constants for the reaction between N-aryl triazolium N-heterocyclic carbene (NHC) precatalysts and substituted benzaldehyde derivatives to form 3-(hydroxybenzyl)azolium adducts under both catalytic and stoichiometric conditions have been measured. Kinetic analysis and reaction profile fitting of both the forward and reverse reactions, plus onwards reaction to the Breslow intermediate, demonstrate the remarkable effect of the benzaldehyde 2-substituent in these reactions and provide insight into the chemoselectivity of cross-benzoin reactions. It takes 2-: Measurement of rate and equilibrium constants for the reaction between N-aryl triazolium NHC precatalysts and substituted benzaldehydes under catalytic and stoichiometric conditions demonstrate the remarkable kinetic and thermodynamic effect of the benzaldehyde 2-substituent in these reactions, potentially providing insight into the chemoselectivity of cross-benzoin reactions.
Oxidations of alkenes with hypervalent iodine reagents: An alternative ozonolysis of phenyl substituted alkenes and allylic oxidation of unsubstituted cyclic alkenes
Atmaca, Ufuk,Usanmaz, Hande K.,?elik, Murat
supporting information, p. 2230 - 2232 (2014/04/17)
Unsaturated CC double bonds with a phenyl substituent can be cleaved with iodylbenzene and iodosylbenzene to give carbonyl compounds. It is believed that the reactions occur via a radical pathway. The allylic oxidation of cyclic alkenes lacking a phenyl substituent was achieved in acetonitrile/water mixture (3:1) also using iodylbenzene and iodosylbenzene.
Enzymatic aerobic alkene cleavage catalyzed by a Mn3+-dependent proteinase A homologue
Rajagopalan, Aashrita,Schober, Markus,Emmerstorfer, Anita,Hammerer, Lucas,Migglautsch, Anna,Seisser, Birgit,Glueck, Silvia. M.,Niehaus, Frank,Eck, Juergen,Pichler, Harald,Gruber, Karl,Kroutil, Wolfgang
, p. 2427 - 2430 (2014/01/06)
New clothes for Mn3+: Aerobic alkene cleavage of styrene-type substrates by Trametes hirsuta is attributed to an enzyme that is dependent on manganese in oxidation state three. The enzyme has a proteinase backbone and binds Mn3+ exclusively via oxygen atoms, in contrast to all known Mn3+ enzymes. Copyright
Mn(III) complexes with tridentate N,N,O-ligands as catalysts for the epoxidation of alkenes
Aghmiz,Mostfa,Iksi,Rivas,Gonzalez,Diaz,El Guemmout,El Laghdach,Echarri,Masdeu-Bulto
, p. 2567 - 2577 (2013/08/23)
Mn(III) complexes with tridentate Schiff bases have been prepared and applied as catalyst precursors in epoxidation of alkenes using iodosobenzene as an oxidant providing high conversions and high selectivities when cyclohexene derivatives were studied.
Biocatalytic cleavage of alkenes with O2 and Trametes hirsuta G FCC 047
Lara, Miguel,Mutti, Francesco G.,Glueck, Silvia M.,Kroutil, Wolfgang
scheme or table, p. 3668 - 3672 (2009/05/07)
Alkenes possessing a C=C double bond adjacent to an aromatic ring were cleaved to yield the corresponding carbonyl compounds by use of molecular oxygen as the sole oxidant and a cell-free extract of the wood-degrading fungus Trametes hirsuta FCC 047 as catalyst. The oxygen pressure required was optimized. Special adapted equipment allowed 96 reactions to be performed in parallel under controlled oxygen pressure. A broad spectrum of aryl-alkenes was successfully converted into the corresponding ketones/aldehydes with excellent chemoselectivity under a controlled oxygen atmosphere (2 bar). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Optimization of a biocatalytic single-step alkene cleavage of aryl alkenes
Mang, Harald,Gross, Johannes,Lara, Miguel,Goessler, Christian,Schoemaker, Hans E.,Guebitz, Georg M.,Kroutil, Wolfgang
, p. 3350 - 3354 (2007/10/03)
The oxidative cleavage of a C{double bond, long}C double bond adjacent to an aryl moiety was achieved in the presence of a protein preparation of Trametes hirsuta G FCC 047 to yield the corresponding aldehydes. Molecular oxygen was the only oxidant required. All positive substrates had a C{double bond, long}C bond conjugated to an aromatic system, all other compounds tested not fulfilling this requirement were non-substrates. The optimum reaction conditions are 20 °C, pH 6-6.5, 15% v/v ethanol as co-solvent at an apparent oxygen pressure of 2 bar.
