15121-89-8Relevant articles and documents
Rhodium-Catalysed Redox Isomerization of Hydroxy Alkynes to Trans Keto and Hydroxy Vinyl Esters. A Short and Stereoselective Synthesis of Dipeptide Isosters
Saiah, M. K. Eddine,Pellicciari, Roberto
, p. 4497 - 4500 (1995)
Tris(triphenylphosphine)Rhodium(I) Chloride in the presence trialkyl phosphine catalyses the isomerization of hydroxy alkynes to unsaturated trans keto and hydroxy esters depending on the nature of the phosphine.Dipeptide isosters were obtained in an efficient manner by the application of this methodology.
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
supporting information, 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.
Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines
Ding, Xiaojuan,Duan, Jindian,Fang, Zheng,Guo, Kai,Li, Zhenjiang,Mao, Yiyang,Rong, Binsen,Xu, Gaochen,Zhang, Lei,Zhu, Ning
supporting information, p. 2532 - 2542 (2020/03/13)
The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.
Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian
, p. 539 - 543 (2019/01/09)
A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.
Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
supporting information, p. 5040 - 5045 (2019/07/03)
(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
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.
A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides
Neuhaus, James D.,Bauer, Adriano,Pinto, Alexandre,Maulide, Nuno
, p. 16215 - 16218 (2018/11/23)
A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions
Gao, Yaru,Ma, Yafei,Xu, Chen,Li, Lin,Yang, Tianjian,Sima, Guoqing,Fu, Zhenqian,Huang, Wei
supporting information, p. 479 - 484 (2017/12/26)
Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and α, β-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities. (Figure presented.).
Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
Xu, Changliang,Bai, Xiaoguang,Xu, Jian,Ren, Jinfeng,Xing, Yun,Li, Ziqiang,Wang, Juxian,Shi, Jingjing,Yu, Liyan,Wang, Yucheng
, p. 4763 - 4775 (2017/02/05)
Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.
Base-Controlled Reactions through an Aldol Intermediate Formed between 2-Oxoaldehydes and Malonate Half Esters
Kumar, Atul,Khan, Shahnawaz,Ahmed, Qazi Naveed
supporting information, p. 4730 - 4733 (2017/09/22)
A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) catalyzed the synthesis of stable decarboxylative aldol products (α-hydroxy ketones), while the Doebner modification procedure resulted in decarboxylative elimination to (E)-α,β-unsaturated esters in good yields. The application of this method in one pot and one pot/two steps with azoles helped to develop regioselective α- and β-azolated products in appreciable yields.
