294886-72-9Relevant 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)
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 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.
