80975-83-3Relevant academic research and scientific papers
Synthesis of Cyclic N-Hydroxylated Ureas and Oxazolidinone Oximes Enabled by Chemoselective Iodine(III)-Mediated Radical or Cationic Cyclizations of Unsaturated N-Alkoxyureas
Peilleron, Laure,Retailleau, Pascal,Cariou, Kevin
supporting information, p. 5160 - 5169 (2019/11/11)
In this study we describe the reactivity of unsaturated N-alkoxyureas in the presence of different combinations of a hypervalent iodine(III) reagent and a bromide source or TEMPO. Three complementary cyclizations can be achieved depending on the reaction conditions. On the one hand, PIFA with pyridinium bromide leads to an oxybromination reaction. On the other hand, bis(tert-butylcarbonyloxy)iodobenzene with tetrabutylammonium bromide or TEMPO triggers aminobromination or aminooxyamination reactions, respectively. Control experiments showed that the three reactions proceed through distinct mechanisms: the first process is ionic while the other two follow a radical manifold. (Figure presented.).
Addition of a B-H Bond across an Amido-Cobalt Bond: CoII-H-Catalyzed Hydroboration of Olefins
Pang, Maofu,Wu, Chengjuan,Zhuang, Xuewen,Zhang, Fanjun,Su, Mincong,Tong, Qingxiao,Tung, Chen-Ho,Wang, Wenguang
, p. 1462 - 1467 (2018/05/24)
This paper describes a well-defined cobalt(II) half-sandwich complex bearing a phosphinoaminato ligand, Cp Co(1,2-Ph2PC6H4NH) (1), that can activate pinacolborane (HBpin) for catalytic terminal hydroboration of olefins. Th
Sequential Metal-Free Thermal 1,3-Dipolar Cycloaddition of Unactivated Azomethine Ylides
Selva, Verónica,Selva, Elisabet,Merino, Pedro,Nájera, Carmen,Sansano, José M.
supporting information, p. 3522 - 3526 (2018/06/26)
The thermal 1,3-dipolar cycloaddition of unactivated azomethine ylides derived from allylamine and aromatic or heteroaromatic aldehydes with maleimides and 1,1- and 1,2-bis(phenylsulfonyl)ethylene affords endo-2,5-trans cycloadducts in moderate to good yi
1,3-allylic strain as a strategic diversification element for constructing libraries of substituted 2-arylpiperidines
Coombs, Thomas C.,Lushington, Gerald H.,Douglas, Justin,Aube, Jeffrey
supporting information; experimental part, p. 2734 - 2737 (2011/05/12)
Flipping diversity: Minimization of 1,3-allylic strain (A1, 3 strain) is a recurring element in the design of a stereochemically and spatially diverse collection of 2-arylpiperidines. A1, 3 strain guides the regioselective addition of nucleophiles and N-substituents leverage A 1, 3 strain to direct each stereoisomer to two different conformer populations, thus doubling the number of library members. Copyright
Comparison of imine to olefin insertion reactions: Generation of five- and six-membered lactams via a nickel-mediated co, olefin, co, imine insertion cascade
Davis, Jason L.,Arndtsen, Bruce A.
experimental part, p. 1896 - 1901 (2011/05/13)
Cationic nickel complexes of the form L2Ni(CH 3)(RN=C(H)R)+ (L2 = bidentate nitrogen donor) have been probed for their ability to mediate olefin and imine migratory insertion reactions. While these complexes do
Catalytic intermolecular hetero-dehydro-diels-alder cycloadditions: Regioand diasteroselective synthesis of 5,6-dihydropyridin-2-ones
Fernandez-Garcia, Jesus Manuel,Fernandez-Rodriguez, Manuel A.,Aguilar, Enrique
supporting information; experimental part, p. 5172 - 5175 (2011/12/04)
A novel catalyzed intermolecular heterodehydro-Diels-Alder reaction between push-pull 1,3-dien-5-ynes and aldimines or silylaldimines is reported. The sequence is promoted both by gold(I) or silver(I) catalysts and leads to the diastereo- and regioselective formation of 5,6- dihydropyridin-2-ones.
Cp2VCl2-catalyzed meso-selective pinacol coupling reaction of aldimines in the presence of chlorosilane and zinc metal
Hatano, Bunpei,Ogawa, Akiya,Hirao, Toshikazu
, p. 9421 - 9424 (2007/10/03)
A catalytic reductive coupling of aldimines was achieved by using a catalyst Cp2VCl2/PhMe2SiCl/Zn system. The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereoselectivity of the coupling products was investigated in detail. As a result, the present Cp2VCl2-catalyzed reductive coupling of aldimines in the presence of PhMe2-SiCl and zinc metal provided the corresponding 1,2- diamines in good yield with high meso selectivity (up to 92% meso), while the reductive coupling of aldehydes, ketones, and aldimines by the hitherto known catalytic methods leads to the preferential formation of dl isomers of the coupling products.
A new synthesis of 2-methyleneaziridines
De Kimpe, Norbert,De Smaele, Dirk,Sakonyi, Zsolt
, p. 2448 - 2452 (2007/10/03)
A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.
Photolysis of 3-chloro-3-aryldiazirines in the presence of amines and allyl alcohol
Liu,Romashin,Venkatachalam
, p. 1961 - 1965 (2007/10/02)
When photolysis of arylchlorodiazirines is performed in the presence of either alkyl- or allyl-substituted amines, either N-alkyl- or N-allyl-substituted amines result as the sole high-yield (64-93%) products. Photolysis in the presence of phenylally-lami
