1121-44-4Relevant academic research and scientific papers
O-benzoylhydroxylamines as alkyl nitrene precursors: Synthesis of saturated N-heterocycles from primary amines
Noda, Hidetoshi,Asada, Yasuko,Shibasaki, Masakatsu
supporting information, p. 8769 - 8773 (2020/10/12)
We introduce O-benzoylhydroxylamines as competent alkyl nitrene precursors. The combination of readily available, stable substrates and a proficient rhodium catalyst provides a straightforward means for the construction of various pyrrolidine rings from the corresponding primary amines. Preliminary mechanistic investigation suggests that the structure of the nitrene precursor plays a role in determining the nature of the resulting reactive intermediate.
Triiodide-Mediated δ-Amination of Secondary C?H Bonds
Wappes, Ethan A.,Fosu, Stacy C.,Chopko, Trevor C.,Nagib, David A.
supporting information, p. 9974 - 9978 (2016/08/16)
The Cδ?H amination of unactivated, secondary C?H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3?)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3?, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.
A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
, p. 440 - 442 (2015/12/30)
Diphenyloxapyrrolizidines, products of the reaction between proline and benzaldehyde, are convenient building blocks for synthesizing 2-substituted pyrrolidines. The opening of their oxazolidine ring by treatment with Grignard reagents has been performed
High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines
Libendi, Samuel S.,Demizu, Yosuke,Matsumura, Yoshihiro,Onomura, Osamu
, p. 3935 - 3942 (2008/09/20)
N-Protecting groups of α-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into α′-methoxylated compounds, while N-cyano derivatives changed into α-methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the α-methoxylated compounds protected with cyano group afforded α,α-disubstituted cyclic amines.
REGIOSPECIFIC OXIDATIVE CYCLIZATION OF N-METHYLSULFONYLAMINES INTO PYRROLIDINES
Nikishin, Gennady I.,Troyansky, Emmanuil I.,Lazareva, Margarite I.
, p. 4279 - 4288 (2007/10/02)
In the framework of the approach to remote oxidative functionalization of organic compounds of various classes, which is currently under exploration by us and which is based on reactions of element-centred free radicals, the regiospecific oxidative cyclization of N-methylsulfonylalkylamines 3 into N-methylsulfonylpyrrolidines 4 has been accomplished.The more facile isomerisation of intermediate sulfonamidyl radicals 8 with 1,5-H shift in comparison with their carboxamidyl analogues 16 is, in our opinion, the chemical proof of different electronic configurations of radicals 8 (? structure) and 16 (predominantly ? structure) generated under identical conditions using Na2S2O8-CuCl2 system.
