294886-74-1Relevant 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.
, 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.
Continuous Flow Synthesis of Dimethylalkynylaluminum Reagents
Piccardi, Riccardo,Coffinet, Anais,Benedetti, Erica,Turcaud, Serge,Micouin, Laurent
, p. 3272 - 3278 (2016/09/12)
A new process for the synthesis of dimethylalkynylaluminum reagents under flow conditions is described. It involves a base-catalyzed alumination of terminal alkynes using a resin-supported organocatalyst. Final organometallic species are obtained in solution, and can further react with various aldehydes or nitrones.
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
supporting information, 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
Trimethylaluminum-assisted alkynylation of nitrones
Bunlaksananusorn, Tanasri,Lecourt, Thomas,Micouin, Laurent
, p. 1457 - 1459 (2008/02/02)
Reaction of nitrones with terminal alkynes occurs in the presence of 1 equiv of trimethylaluminum and leads to the corresponding propargylic hydroxylamines in yields ranging from 49 to 90%.
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.
Addition of functional vinylzinc reagents to nitrones: Synthesis of (E)-N-allylhydroxylamines and their rearrangement into (E)-O-allylhydroxylamines
Pandya,Garcon,Chavant,Py,Vallee
, p. 1806 - 1807 (2007/10/03)
The vinylzinc reagents derived from hydrozirconation of alkynes and transmetallation add readily to nitrones to yield pure (E)-N-allylhydroxylamines; some of these rearrange into O-allylhydroxylamines.
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.
