Refernces
10.1016/j.tetlet.2014.02.046
The study presents an innovative method for the 1,4-addition of arylboronic acids to α,β-unsaturated substrates using nickel(I) complexes as catalysts. The nickel(I) species were generated in situ from Ni(PPh3)2Cl2 with the aid of activated iron, and the catalytic system was combined with NN'-bis(4-fluorobenzylidene) ethane-1,2-diamine (BFBED). The reaction is completed without the need for a base, but the presence of potassium iodide is essential. The study suggests a possible Ni(I)–Ni(III) catalytic cycle mechanism and demonstrates the efficiency of the method with yields up to 76%. The scope of the reaction was explored with various substrates and arylboronic acids, showing no significant influence from electron-withdrawing or electron-donating groups. The work provides a valuable contribution to the field of cross-coupling reactions, offering a more environmentally benign and cost-effective alternative to traditional noble metal catalysts.
10.1021/ol200924e
The research focuses on the organocatalytic construction of all-carbon quaternary stereocenters through Michael addition with β-ketoamides, highlighting the cooperative role of the secondary amido group in controlling reactivity and selectivity. The study explores the enantioselective construction of quaternary centers, a challenging task in the synthesis of complex natural and pharmaceutical products. Experiments involved the conjugate addition of various R-substituted β-ketoamides (such as 1a to 1g) to unsaturated carbonyls like methylvinylketone (2a) and enals, using bifunctional catalysts (specifically the Takemoto Thiourea Catalyst, TUC, 3f). The reactions were optimized in terms of catalyst selection, solvent, and reaction conditions to achieve high yields and enantioselectivity, with toluene emerging as the best solvent and the catalyst 3f providing the highest enantiomeric excess (ee) of up to 99%. Analyses included TLC, HPLC on a chiral stationary phase, 1H NMR, single crystal X-ray analysis for absolute configuration determination, and Vibrational Circular Dichroism (VCD) spectra for enantiomeric confirmation. The study also proposed a transition-state model to explain the observed enantioselective outcome and demonstrated the synthetic potential of the products through a domino Michael/spirolactamization sequence leading to chiral spiro-heterocycles.
10.1016/S0957-4166(01)00391-3
The study in the provided scholarly article focuses on the synthesis of specific octahydroquinolin-7-ones, which are compounds derived from aspidosperma alkaloids and are important in asymmetric synthesis. The researchers synthesized the enamine (?)-(1’S)-5-ethyl-1-(1’-phenylethyl)-1,2,3,4-tetrahydropyridine 4 and used it to create (?)-(1’S,4aS,8aR)- and (+)-(1’S,4aR,8aS)-4a-ethyl-1-(1’-phenylethyl)-octahydroquinolin-7-ones 5 and 6. Key chemicals used in the study include (?)-(S)-1-phenylethylamine, 4-formyl-hexanoic acid methyl ester, LiAlH4/THF for reduction, and methyl vinyl ketone (MVK) in the presence of KOH/18-crown-6/methanol. These chemicals served various purposes, such as starting materials for the synthesis, a reducing agent, and reagents for the condensation reaction to form the desired octahydroquinolin-7-ones. The study also reports an X-ray study of compound 6, which confirmed the cis-fused ring structure and absolute configurations of the stereogenic centers. The purpose of these chemical syntheses was to explore the applications of 3,4-dihydro-1H-pyridin-2-ones in asymmetric synthesis and to prepare compounds 5 and 6 with specific stereochemistries.
10.1016/0040-4020(89)80028-6
The research details the development of new carbon-carbon bond forming reactions using catalytic amounts of tin(II) reagents in organic synthesis. The study focused on the aldol reaction, a fundamental carbon-carbon bond forming process, and the Michael reaction, aiming to achieve high stereoselectivity with minimal reagent usage. The researchers successfully developed a catalytic aldol reaction using tin(II) enolate, which was generated from a,b-unsaturated ketones, aldehydes, and ethylthiotrimethylsilane in the presence of catalytic tin(II) triflate sulfide. They also realized a catalytic asymmetric Michael reaction using tin(II) enethiolate and a catalytic amount of tin(III) triflate-chiral diamine complex. The chemicals central to this research include tin(II) triflate, ethylthiotrimethylsilane, benzaldehyde, methyl vinyl ketone, and chalcone, among others. The conclusions highlight the successful development of catalytic asymmetric reactions with moderate to good enantioselectivity, marking a significant advancement in modern organic synthesis.
10.1016/S0040-4020(02)01518-1
The study focuses on the synthesis of 3-substituted-4-hydroxyquinoline N-oxides from Baylis–Hillman adducts derived from o-nitrobenzaldehydes. The key chemicals used in the study include trifluoroacetic acid, trifllic acid, and various Baylis–Hillman adducts such as 1b–f, which are derived from methyl vinyl ketone, phenyl vinyl sulfone, and ethyl acrylate. These chemicals serve the purpose of facilitating the reaction that yields the desired quinoline N-oxide derivatives. The study also explores the reaction mechanism, suggesting that N-hydroxyisoxazoline acts as a key intermediate in the process. The use of triflic acid was found to increase the acidity of the reaction medium, which was crucial for obtaining the quinoline N-oxides in reasonable yields. The study provides experimental evidence supporting the proposed reaction mechanism and successfully synthesizes several 3-substituted-4-hydroxyquinoline N-oxides, which are valuable synthetic intermediates.
10.1021/jo00805a002
The study investigates the reactions of 2-diazoacenaphthenone (1) with various olefins and acetylenes. The researchers found that 1 did not decompose in boiling benzene or toluene but underwent copper-catalyzed thermolysis in boiling toluene to form biacenedione. In boiling xylene, 1 produced biacenedione and a trace amount of acenaphthenequinone ketazine. When 1 reacted with olefins like ethyl acrylate, acrylonitrile, ethyl a-bromoacrylate, and methyl vinyl ketone in refluxing benzene, it yielded spiro[acenaphthenone-2,1'-cyclopropanes] (3a-d, 4a-c, 7) with two stereoisomers for some reactions. Reactions with acrolein, phenylacetylene, and diethyl acetylenedicarboxylate led to the formation of 2'-hydroxymethylspiro[acenaphthenone-2,1'-cyclopropanes] (5, 6) and spiro[acenaphthenone-2,3'(3'H)-pyrazoles] (9, 10). The study also explored the reaction of 1 with bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, producing spiro[acenaphthenone-2,3'-tricyclooctanedicarboxylic anhydride] (8). The researchers used various analytical techniques to confirm the structures and properties of the synthesized compounds.
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