294886-82-1Relevant academic research and scientific papers
Zinc mediated direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones and mechanistic insight
Das, Prasanta,Hamme, Ashton T.
supporting information, p. 1086 - 1089 (2017/03/02)
A Lewis acid catalyzed direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones in the presence of aqueous Zn(II)-salts has been described. This investigation also provides a novel observation for the stoichiometric role of Zn-halides over what is known to date for catalytic processes. A thorough mechanistic study has been established based on the experiment using18O-labeled water in optimized reaction conditions; the incorporation of18O in the desired product was also substantiated by HRMS. This methodology is also a mild, inexpensive, and an efficient approach for this unusual conversion.
Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines
Chandrasekhar,Ahn, Sewon,Ryu, Jae-Sang
, p. 6740 - 6749 (2016/08/16)
New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.
4-Bromo-2,3-dihydroisoxazoles: synthesis and application in halogen-lithium exchange reactions
Kle??íková, Lucia,Doháňo?ová, Jana,Fischer, Róbert
, p. 6112 - 6115 (2015/08/03)
Abstract The synthesis of novel types of 4-bromo-2,3-dihydroisoxazoles using pyridinium tribromide in the presence of base is described. Reactivity of the initial substrates and the yields depend on the substituent at C3. To demonstrate a practical scope
A Lewis acid/metal amide hybrid as an efficient catalyst for carbon-carbon bond formation
Yamashita, Yasuhiro,Saito, Yuki,Imaizumi, Takaki,Kobayashi, Shu
, p. 3958 - 3962 (2014/10/15)
While Lewis acids and metal amides are among the most frequently used metal species, they are believed to be incompatible when combined. Here we describe a Lewis acid/metal amide hybrid, which contains electron-withdrawing groups and basic and bulky nitro
One-pot stereoselective synthesis of 2-acylaziridines and 2-acylpyrrolidines from N-(propargylic)hydroxylamines
Miyamoto, Yoshiaki,Wada, Norihiro,Soeta, Takahiro,Fujinami, Shuhei,Inomata, Katsuhiko,Ukaji, Yutaka
, p. 824 - 831 (2013/05/21)
The stereoselective direct transformation of N-(propargylic)hydroxylamines into cis-2-acylaziridines was achieved by the combined use of AgBF4 and CuCl. Copper salts were found to promote the transformation of the intermediary 4-isoxazolines in
Selective transformation of N-(propargylic)hydroxylamines into 4-isoxazolines and acylaziridines promoted by metal salts
Wada, Norihiro,Kaneko, Kentaro,Ukaji, Yutaka,Inomata, Katsuhiko
scheme or table, p. 440 - 442 (2011/06/23)
Cyclization of N-(propargylic)hydroxylamines catalyzed by AgBF4 afforded the corresponding 4-isoxazolines in good yields. Copper salts were found to promote the further transformation to acylaziridines. The combined use of AgBF4 and CuCl realiz
Reduction of 2,3-dihydroisoxazoles to β-amino ketones and β-amino alcohols
Aschwanden, Patrick,Kvaerno, Lisbet,Geisser, Roger W.,Kleinbeck, Florian,Carreira, Erick M.
, p. 5741 - 5742 (2007/10/03)
(Chemical Equation Presented) We report the reduction of 2,3-dihydroisoxazoles to β-amino ketones and β-amino alcohols. The latter are obtained in high diastereoselectivity with preference for the syn isomer.
Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction
Aschwanden, Patrick,Frantz, Doug E.,Carreira, Erick M.
, p. 2331 - 2333 (2007/10/03)
(equation presented) A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisubstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mol %) of ZnI2 and DMAP is reported. The methodology provides a mild new approach to this useful class of substituted heterocycles that complements extant methods. The unique reactivity of the propargylic N-hydroxylamine substrates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.
