19522-28-2Relevant academic research and scientific papers
Sodium bicarbonate-catalyzed stereoselective isomerizations of electron-deficient propargylic alcohols to (Z)-enones
Sonye, John P.,Koide, Kazunori
, p. 1846 - 1848 (2007)
Redox isomerization is a synthetically important process because it creates two new functional groups in the product, among which is the isomerization of propargylic alcohols to conjugated enones. Although E-enones have been prepared by this approach, Z-e
Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers
De Bruin, Bas,De Zwart, Felix J.,Li, Zirui,Mathew, Simon,Wolzak, Lukas A.,Zhou, Minghui
, p. 20501 - 20512 (2021/12/03)
The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.
A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
supporting information, p. 5074 - 5077 (2018/05/26)
A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins
Kan, S. B. Jennifer,Maruyama, Hiroki,Akakura, Matsujiro,Kano, Taichi,Maruoka, Keiji
supporting information, p. 9487 - 9491 (2017/08/01)
A chiral-amine-catalyzed enantioselective and diastereodivergent method for aldehyde addition to electron-deficient olefins is presented. Hydrogen bonding was used as a control element to achieve unusual anti selectivity, which was further elucidated through mechanistic and computational studies.
Remote activation of the nucleophilicity of isatin
Zari, Sergei,Kudrjashova, Marina,Pehk, Tonis,Lopp, Margus,Kanger, Tonis
supporting information, p. 1740 - 1743 (2014/04/17)
The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.
Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents
Kang, Wang,Du, Xingqiong,Wang, Lanzhi,Hu, Lijuan,Dong, Yuhuan,Bian, Yanqing,Li, Yuan
, p. 1305 - 1314 (2013/11/06)
Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright
Organic base-catalyzed stereoselective isomerizations of 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester to (E)- and (Z)-4-oxo-4-phenyl-but-2-enoic acid methyl esters
Sonye, John P.,Koide, Kazunori
, p. 599 - 602 (2007/10/03)
We have developed a 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed isomerization of 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester to (E)-4-oxo-4-phenyl-but-2-enoic acid methyl ester and an N,N- diisopropylethylamine-catalyzed isomerization of the same
On the mechanism of DABCO-catalyzed isomerization of γ-hydroxy- α,β-alkynoates to γ-oxo-α,β(E)-alkenoates
Sonye, John P.,Koide, Kazunori
, p. 199 - 202 (2007/10/03)
Since the discovery of organic base-catalyzed isomerization of γ-hydroxy-α,β-acetylenic esters to γ-oxo-α,β- trans-alkenyl esters in 1949, the mechanism has not been elucidated. This study shows that the mechanism involves cumulene formation, protonation
Base-catalyzed stereoselective isomerization of electron-deficient propargylic alcohols to E-enones
Sonye, John P.,Koide, Kazunori
, p. 6254 - 6257 (2007/10/03)
We have developed highly stereoselective methods to isomerize electron-deficient propargylic alcohols to E-enones under mild conditions (EWG = electron-withdrawing group). Among weak bases we screened, catalytic (10-20 mol %) 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to be effective in most cases. When the substrate is conjugated with an amide, the addition of sodium acetate catalyzed the isomerization.
Polarographic behavior of methyl 4-aryl-2,4-dioxobutanoates
Posyagin,Posyagina,Zalesov,Kataev
, p. 1574 - 1577 (2007/10/03)
Polarographic reduction of methyl 4-aryl-2,4-dioxobutanoates in aqueous 2-propanol involves two cathodic waves and yields methyl 4-aryl-2,4-dihydroxybutanoates.
