20147-43-7Relevant academic research and scientific papers
Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement
Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun
supporting information, p. 5506 - 5511 (2021/07/31)
Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.
NO cations as highly efficient catalysts for carbon-carbon bond forming reactions
Yamashita, Yasuhiro,Kobayashi, Shue
supporting information; experimental part, p. 678 - 679 (2011/04/22)
NO cations were found to be a highly effective catalysts in several carbon-carbon bond forming reactions. For example, [3 + 2] cycloadditions of nitrones or azomethine imines with vinyl ethers proceeded in the presence of 0.1-1 mol % of the NO cation to afford the desired adducts in high yields. Copyright
Ti(IV) promoted 1,3-dipolar cycloaddition of nitrones to vinyl ethers
Bayon, Pau,De March, Pedro,Figueredo, Marta,Font, Josep
, p. 15691 - 15700 (2007/10/03)
The 1,3-dipolar cycloaddition of nitrones to vinyl ethers is accelerated by Ti(IV) species. The efficiency of the catalyst parallels its complexation capacity. The use of Ti((i)prO)2Cl2 favours the formation of trans cycloadducts, presumably through an endo bidentate complex, in which the metal atom is simultaneously coordinated to the vinyl ether and to the cyclic nitrone or the Z isomer of the acyclic nitrones.
Synthesis of 4-alkoxy and 3-nitro substituted isoxazolidines by catalyzed 1,3-dipolar cycloaddition reactions of nitrones with vinyl ethers and nitro alkenes
Meske, Michael
, p. 426 - 433 (2007/10/03)
1,3-Dipolar cycloadditions of the C-phenyl-N-alkylnitrones 1,3 and the C,N-diphenylnitrone (2) with vinyl ethers 5,6 are strongly catalyzed by chiral oxazaborolidines derived from N-arylsulfonyl substituted L-α-amino acids valine and tert-butyl leucine an
1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines
Seerden, Jean-Paul G.,Boeren, Mike M. M.,Scheeren, Hans W.
, p. 11843 - 11852 (2007/10/03)
The 1,3-dipolar cycloaddition reactions of various Z- and E-nitrones with ethyl vinyl ether and 2,3-dihydrofuran are catalyzed by 20 mol% of chiral oxazaborolidines at room temperature. The effect of high pressure on these reactions is discussed.
Ring-opening of isoxazolidine system: Homologation of 3-aryl into 3-styryl nitrones via intermediate 5-hydroxy-isoxazolidines
Chiacchio, Ugo,Liguori, Angelo,Romeo, Giovanni,Sindona, Giovanni,Uccella, Nicola
, p. 9473 - 9482 (2007/10/02)
High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.
