875062-82-1Relevant academic research and scientific papers
Strained enamines as versatile intermediates for stereocontrolled construction of nitrogen heterocycles
Chen, Gang,Sasaki, Mikio,Li, Xinghan,Yudin, Andrei K.
, p. 6067 - 6073 (2006)
This contribution assesses the synthetic utility of molecules that impose conformational constrains onto aziridine-derived enamines. Synthetically versatile [3.1.0] and [4.1.0] bicyclic enamines have been prepared by intramolecular oxidative cycloamination of aziridine-containing olefins. This process is initiated by N-bromosuccinimide followed by base-mediated elimination of HBr to afford highly strained exo-bicyclic enamines. In addition, intramolecular aziridine addition to aldehyde functionality was found to afford the [3.1.0] and [4.1.0] bicyclic hemiaminals. These routes highlight possibilities for chemoselective oxidative transformations of aziridine-containing precursors without nitrogen protection/deprotection steps. The resulting products provide straightforward synthetic entries into a wide range of pyrrolidine- and piperidine-containing heterocycles that are positioned toward subsequent transformations via aziridine ring opening.
Facile preparation of allyl amines and pyrazoles by hydrazinolysis of 2-ketoaziridines
Chen, Gang,Sasaki, Mikio,Yudin, Andrei K.
, p. 255 - 259 (2007/10/03)
Allyl amines and pyrazoles can be obtained by hydrazinolysis of 2-ketoaziridines. A variety of aziridines, including N-unprotected, N-substituted, as well as bicyclic enamine and aminal type, can be transformed into diversely substituted linear or cyclic products. The hydrazinolysis of homochiral aziridines proceeds without racemization.
Oxidative Cycloamination of Olefins with Aziridines as a Versatile Route to Saturated Nitrogen-Containing Heterocycles
Sasaki, Mikio,Yudin, Andrei K.
, p. 14242 - 14243 (2007/10/03)
Highly reactive [5,3] and [6,3] bicyclic aziridines can be readily prepared from the corresponding NH aziridines and N-bromosuccinimide by intramolecular oxidative cycloamination of olefins. These compounds, including surprisingly stable exo-methylene bicyclic aziridines, provide versatile synthetic entries into a wide range of pyrrolidine- and piperidine-containing heterocycles. Copyright
