183005-97-2Relevant academic research and scientific papers
Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition
Khoroshunova, Yulia V.,Morozov, Denis A.,Taratayko, Andrey I.,Gladkikh, Polina D.,Glazachev, Yuri I.,Kirilyuk, Igor A.
, p. 2036 - 2042 (2019)
Sterically shielded nitroxides of the pyrrolidine series have shown the highest resistance to reduction. Here we report the synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of a pent-4-enyl group to the nitrone carbon followed by an intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. The kinetics of reduction of the new nitroxides with ascorbate were studied and compared to those of previously published (1S,2R,3′S,4′S,5′S,2″R)-dispiro[(2-hydroxymethyl)cyclopentan-1,2′-(3′,4′-di-tert-butoxy)pyrrolidine-5′,1″-(2″-hydroxymethyl)cyclopentane]-1′-oxyl (1).
Radical cyclization of α-allenic ketone: A new approach to the synthesis of (±)-α-chamigrene
Chen, Yao-Jung,Wang, Chi-Ying,Lin, Wen-Yuan
, p. 13181 - 13188 (2007/10/03)
A regioselective cyclization of ε-alkyl radicals attacking on the sp-carbon of α-allenic ketone to construct a spiro[5.5]undecane skeleton has been studied, and a new approach to the synthesis of (±)-α-chamigrene 22 is also reported.
