124413-92-9Relevant academic research and scientific papers
An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate
Mayer, Michael F.,Wang, Qinwei,Hossain, M. Mahmun
, p. 78 - 83 (2001)
The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.
Synthesis of aziridines from imines and ethyl diazoacetate in room temperature ionic liquids
Sun, Wei,Xia, Chun-Gu,Wang, Hong-Wang
, p. 2409 - 2411 (2003)
The synthesis of aziridines from imines and ethyl diazoacetate in room temperature ionic liquids is reported. The reactions proceed readily under mild conditions with high cis selectivities and high yields.
Aziridine synthesis in protic media by using lanthanide triflates as catalysts
Xie, Wenhua,Fang, Jianwen,Li, Jun,Wang, Peng George
, p. 12929 - 12938 (1999)
Ln(OTf)3-catalyzed aziridine synthesis from imines and diazo compounds was studied in a variety of protic media. The reactions proceeded readily under mild conditions and were highly selective, affording predominantly cis aziridines. The imines used were typically those derived from aromatic aldehydes and aromatic amines, with either electron-donating or electron- withdrawing substituents. N-benzyl aryl aldimines and imines derived from aromatic amines and hindered aliphatic aldehydes were also found to work well. Among the three diazo compounds examined, ethyl diazoacetate (EDA) and 3-nitrophenyl diazomethane were effective reagents for the aziridination. However, the reactions of ethyl diazoacetoacetate failed to give any desired product. Six lanthanides triflates as well as Sc(OTf)3 and Y(OTf)3 were tested as catalyst in the aziridination reaction. The formation of the by- products was also discussed.
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines: A highly diastereoselective synthesis of cis-aziridine carboxylates
Sengupta,Mondal
, p. 6245 - 6248 (2000)
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines give aziridine carboxylates under mild conditions, low catalyst loading and with high cis-selectivity. (C) 2000 Elsevier Science Ltd.
Divergent pathways in the reaction of fischer carbenes and palladium
Lopez-Alberca, Maria P.,Mancheno, Maria J.,Fernandez, Israel,Gomez-Gallego, Mar,Sierra, Miguel A.,Torres, Rosario
, p. 1757 - 1759 (2007)
The Pd-catalyzed reaction of β-arylaminochromium(0) carbene complexes produces by transmetalation the first isolated and X-ray structurally characterized bis-Pd(II) carbene complex, as well as other alternative reaction pathways, such as the oxidative addition-transmetalation sequence, not seen before in this chemistry.
Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution
Lei, Tao,Liang, Ge,Cheng, Yuan-Yuan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 5385 - 5389 (2020)
Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments and spectroscopic studies demonstrated a reductive quenching pathway of cobaloxime catalyst to produce phosphinoyl radical, which underwent cross-coupling with various enamines (and enamides) to give diverse β-phosphinoyl products in good to excellent yields. More interestingly, Z/E mixture of acyclic enamines could convert into single Z-products with good reactivity.
Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines
Chen, Zhiwei,Shi, Guang,Tang, Wei,Sun, Jie,Wang, Wenxing
supporting information, p. 951 - 955 (2021/02/03)
A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.
Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
Cai, Yichao,Chen, Chunxia,Chen, Xin,Liu, Yajie,Peng, Jinsong,Song, Zirui,Sun, Peng,Yang, Jiaojiao
, p. 75 - 84 (2019/12/26)
Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The i
Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes
Benítez-Puebla, Luis J.,López, Julio,Flores-álamo, Marcos,Cruz, David Cruz,Pe?a-Cabrera, Eduardo,Delgado, Francisco,Tamariz, Joaquín,Vázquez, Miguel A.
supporting information, p. 6571 - 6578 (2019/10/22)
The results of a study of the reactivities of alkynyl Fischer carbenes in the syntheses of diazaborinine derivatives 7a-i are reported. The strategy employed included the use of β-amino-α,β-unsaturated carbenes (3a–j) with different amines in order to determine the scope of a previously unknown catalytic reaction in the presence of copper salts and anilines. The reaction was highly stereoselective, yielding (Z)-isomers of the β-amino-1-azadiene framework as the main products (4a–o). As an extension of this research, the compounds 4a–o proved to be suitable precursors for the syntheses of diazaborinine scaffolds in good yields (7a-i).
Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols
Dong, Mengxian,Wang, Jie,Wu, Shijie,Zhao, Yang,Ma, Yangyang,Xing, Yongfei,Cao, Fei,Li, Longfei,Li, Zhenqiu,Zhu, Huajie
supporting information, p. 4602 - 4610 (2019/08/30)
Axial N-O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2- and 1,4-transfer hydrogenations of total 26 ketimines and β-enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. Interestingly, a mixture of (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide and (aR)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide was also able to provide high enantioselectivities up to 95% that is the same as that using pure (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. A plausible catalytic mechanism was suggested and total four kinds of transition states (TS) including almost 60 TS structures were investigated using density functional theory (DFT) with different basis sets such as 6-311G(2d,p). The predicted activation energy data are consistent with the experimental results. (Figure presented.).
