484068-19-1Relevant academic research and scientific papers
Stereoselective cyclization reactions of IBX-generated alkoxyamidyl radicals
Janza, Birgit,Studer, Armido
, p. 6991 - 6994 (2005)
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.
Palladium-Catalyzed Ring-Forming Alkene Aminoaroylation of Unsaturated Hydrazones and Sulfonamides
Chen, Jun,Yang, Meng-Nan,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information, p. 3314 - 3318 (2018/06/11)
The first example of a Pd(OAc)2-catalyzed ring-forming alkene aminoaroylation of unsaturated hydrazones and sulfonamides is described. This protocol features the use of diaryliodonium salts as both oxidants and aryl sources, thus enabling mild
Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters
Malkov, Andrei V.,Barlog, MacIej,Miller-Potucka, Lucie,Kabeshov, Mikhail A.,Farrugia, Louis J.,Kocovsky, Pavel
supporting information; experimental part, p. 6873 - 6884 (2012/07/17)
Enantiopure, Boc-protected alkoxyamines 12 and 13, derived from the readily available homoallylic alcohols 4 via a reaction that involves either inversion or retention of configuration, undergo a diastereoselective Pd-catalyzed ring-closing carbonylative
Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation
Karyakarte, Shuklendu D.,Smith, Thomas P.,Chemler, Sherry R.
, p. 7755 - 7760 (2012/10/29)
Isoxazolidines are useful in organic synthesis, drug discovery, and chemical biology endeavors. A new stereoselective synthesis of methyleneoxy-substituted isoxazolidines is disclosed. The method involves copper-catalyzed aminooxygenation/cyclization of N
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
Influence of hydroxylamine conformation on stereocontrol in Pd-catalyzed isoxazolidine-forming reactions
Lernen, Georgia S.,Giampietro, Natalie C.,Hay, Michael B.,Wolfe, John P.
supporting information; experimental part, p. 2533 - 2540 (2009/08/07)
Palladium-catalyzed carboamination reactions between N-Boc-O-(but-3-enyl) hydroxylamine derivatives and aryl or alkenyl bromides afford cis-3,5- and trans-4,5-disubstituted isoxazolidines in good yield with up to >20:1 dr. The diastereoselectivity observe
Palladium-catalyzed sequential one-pot reaction of aryl bromides with O-homoallylhydroxylamines: Synthesis of N-aryl-β-amino alcohols
Peng, Jinsong,Jiang, Dahong,Lin, Wenqing,Chen, Yuanwei
, p. 1391 - 1396 (2008/01/03)
The palladium-catalyzed sequential one-pot N-arylation-carbo-amination-C- arylation of O-homoallylhydroxylamines with two different aryl bromides provides rapid entry to differentially arylated N-aryl-3-arylmethylisoxazolidines in good yields with excelle
Palladium(0)-catalyzed cascade one-pot synthesis of isoxazolidines
Dongol, Krishna Gopal,Tay, Boon Ying
, p. 927 - 930 (2007/10/03)
A highly diastereoselective cascade reaction protocol has been developed for the synthesis of isoxazolidine derivatives utilizing aryl halides, O-homoallyl hydroxylamine and palladium(0) in a one-pot reaction.
Stereoselective electrophilic cyclisation of O-homoallyl hydroxylamine derivatives
Janza, Birgit,Studer, Armido
, p. 2117 - 2123 (2007/10/03)
Electrophilic cyclisations of various O-homoallyl hydroxylamine derivatives are discussed. Non-protected O-homoallyl hydroxylamines undergo oxidative cyclisations to isoxazolines. The new isoxazoline synthesis comprises an initial electrophilic cyclisatio
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
