484068-29-3Relevant academic research and scientific papers
O-Isocyanates as Uncharged 1,3-Dipole Equivalents in [3+2] Cycloadditions
Allen, Meredith A.,Beauchemin, André M.,Ivanovich, Ryan A.
, p. 23188 - 23197 (2020)
1,3-Dipoles are commonly used in [3+2] cycloadditions, whereas isoelectronic uncharged dipole variants remain underdeveloped. In contrast to conventional 1,3-dipoles, uncharged dipole equivalents form zwitterionic cycloadducts, which can be exploited to build further molecular complexity. In this work, the first cycloadditions of oxygen-substituted isocyanates (O-isocyanates) were studied experimentally and by DFT calculations. This unique cycloaddition strategy provides access to a novel class of heterocycle aza-oxonium ylides through intramolecular and intermolecular cycloadditions with alkenes. This allowed a systematic study of the reactivity of the transient aza-oxonium ylide intermediate, which can undergo N?O bond cleavage followed by nitrene C?H insertion, and the formation of β-lactams or isoxazolidinones upon varying the structure of the alkene or O-isocyanate reagents.
Allylation reactions of N,O-heterocycles
Bates, Roderick W.,Tang, Chi H.,Tan, Yuting,Buang, Siti Nurhayati Binte
, p. 2266 - 2268 (2012/11/07)
Iminium ions generated from isoxazolidines and tetrahydro-1,2-oxazines undergo allylation under Sakurai conditions. Allylated isoxazolidines are formed predominantly as the trans isomer, while oxazines are formed exclusively as the cis isomer. Georg Thiem
Stereoselective cyclization reactions of IBX-generated alkoxyamidyl radicals
Janza, Birgit,Studer, Armido
, p. 6991 - 6994 (2007/10/03)
In this paper, a method for the generation of alkoxyamidyl radicals is presented. These N-centered radicals can efficiently be formed starting from the corresponding acylated alkoxyamines using IBX as an oxidant. Stereoselective 5-exo and 6-exo reactions with these N-heteroatom-centered radicals leading to isoxazolidines and [1,2]oxazinanes are discussed. The N-O bond in the heterocycles can readily be cleaved with SmI2 to provide N-acylated 1,3-amino alcohols.
O-alkenyl hydroxylamines: A new concept for cyclofunctionalization
Bates, Roderick W.,Sa-Ei, Kanicha
, p. 4225 - 4227 (2007/10/03)
(equation presented) Treatment of O-homoallylhydroxylamines with palladium(II) and copper(II) in the presence of a base, methanol, and carbon monoxide results in the formation of isooxazolidines. An electron-withdrawing group on the hydroxylamine nitrogen
