70197-11-4Relevant academic research and scientific papers
Phenylaziridine as a 1,3-dipole. Application to the synthesis of functionalized pyrrolidines
Ungureanu, Ioana,Bologa, Cristian,Chayer, Said,Mann, Andre
, p. 5315 - 5318 (1999)
Phenylaziridine 1 in the presence of an appropriate Lewis acid reacts as a 1,3-dipole. The cyclocondensation of 1 with DHP in the presence of BF3·Et2O produced the azaoxa[3.2.0] cycloadducts 4a-4b. The reactivity of the corresponding N-tosyliminium ions was explored.
Copper-Catalyzed Carbonylative Synthesis of β-Homoprolines from N-Fluoro-sulfonamides
Wu, Xiao-Feng,Yin, Zhiping,Zhang, Youcan
, p. 1889 - 1893 (2020/03/24)
A new methodology for the carbonylative transformation of N-fluoro-sulfonamides into N-sulfonyl-β-homoproline esters has been described. In the presence of a catalytic amount of Cu(OTf)2, a range of β-homoproline derivatives were prepared in moderate to good yield. The reaction proceeds via the intramolecular cyclization and intermolecular carbonylation of a free carbon radical. Notably, this procedure offers the possibility to build potential functionalized bioactive molecules.
Palladium-catalyzed highly selective intramolecular bromoamination of alkenes: Efficient synthesis of substituted pyrrolidines
Zhang, Jingfang,Wang, Xie,Liu, Yulong,Wang, Xiaoyun,He, Wei
, (2017/05/22)
A new method has been developed for the preparation of substituted pyrrolidines by the palladium-catalyzed intramolecular bromoamination of substituted aminoalkenes. The catalytic system and reaction conditions used for this transformation have been fully optimized. Notably, this reaction exhibits excellent selectivity, affording the pyrrolidine products as single 5-exo-bromoalkylpyrrolidines in excellent yields. Furthermore, this reaction occurs at room temperature under mild conditions, reaching completion within 1?h.
Regioselective copper(II)-mediated bromoamination of unfunctionalized olefins: An efficient route to N-heterocyclic compounds
Liu, Gong-Qing,Ding, Zhen-Ying,Zhang, Li,Li, Ting-Ting,Li, Lin,Duan, Lili,Li, Yue-Ming
supporting information, p. 2303 - 2310 (2014/07/21)
Bromoamination of unfunctionalized olefins was realized under mild conditions using copper(II) bromide (CuBr2) as both reaction promoter and bromine source. The reactions could be carried out under open air at ambient temperature, and both N-alkylated and N-tosylated substrates could be converted to the corresponding N-heterocyclic compounds in high regioselectivity and good isolated yields. A variety of biologically important structures could be obtained via subsequent nucleophilic substitution reactions.
Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination
Brenzovich Jr., William E.,Benitez, Diego,Lackner, Aaron D.,Shunatona, Hunter P.,Tkatchouk, Ekaterina,Goddard III, William A.,Toste, F. Dean
supporting information; experimental part, p. 5519 - 5522 (2010/09/05)
(Chemical equation presented) Gold-ilocks and the 3 mol% catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold (I)/gold(III) and a bimolecular reductive elimination for the key C-C bond-forming step is proposed, dppm= bis(diphenylphosphanyl) methane.
NHC-Catalyzed intramolecular redox amidation for the synthesis of functionalized lactams
Thai, Karen,Wang, Li,Dudding, Travis,Bilodeau, Francois,Gravel, Michel
supporting information; experimental part, p. 5708 - 5711 (2011/03/19)
A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.
Scandium triflate-catalyzed 1,3-dipolar cycloaddition of aziridines with alkenes
Yadav,Reddy,Pandey, Sushil Kumar,Srihari, P.,Prathap, I.
, p. 9089 - 9092 (2007/10/03)
Phenyl aziridines undergo 1,3-dipolar cycloaddition efficiently with olefins such as cyclic enol ethers and allyltrimethylsilane in the presence of a catalytic amount of Sc(OTf)3 at ambient temperature to afford the corresponding pyrrolidine derivatives in high yields with high regioselectivity.
Palladium-Catalyzed Cyclization of ω-Olefinic Tosamides. Synthesis of Nonaromatic Nitrogen Heterocycles
Hegedus, Louis S.,McKearin, James M.
, p. 2444 - 2451 (2007/10/02)
The cyclization of aliphatic amino olefins to nonaromatic nitrogen heterocycles nas been accomplished by conversion of the amine to the corresponding p-toluenesulfonamide, followed by Pd(II)-catalyzed intramolecular amination of the olefin.The resulting t
