81555-44-4Relevant academic research and scientific papers
Oxidative Cycloamination of Olefins with Aziridines as a Versatile Route to Saturated Nitrogen-Containing Heterocycles
Sasaki, Mikio,Yudin, Andrei K.
, p. 14242 - 14243 (2003)
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
Strained enamines as versatile intermediates for stereocontrolled construction of nitrogen heterocycles
Chen, Gang,Sasaki, Mikio,Li, Xinghan,Yudin, Andrei K.
, p. 6067 - 6073 (2007/10/03)
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.
Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines
Dalili, Shadi,Yudin, Andrei K.
, p. 1161 - 1164 (2007/10/03)
(Chemical Equation Presented) Straightforward methods for palladium-catalyzed alkenylation of aziridines with alkenyl halides and copper-catalyzed alkenylation of aziridines with alkenyl boronic acids have been developed. This methodology offers attractive alternatives to the known methods requiring activated alkenyl halides and acetylenes. A wide variety of N-alkenyl aziridines containing substituents other than electron-withdrawing substituants such as cyano groups and sulfones have been synthesized in good yields. Furthermore, these N-alkenyl aziridines exhibit quite a different reactivity from conventional enamines, as demonstrated by their reactivity.
Reductive Cyclization of Mercurial Enones
Danishefsky, Samuel,Chackalamannil, Samuel,Uang, Biing-Jiun
, p. 2231 - 2232 (2007/10/02)
A series of enones containing pendant isolated olefinic linkages was prepared.Solvomercuration could be conducted specifically at the isolated double bond.Treatment of these systems with sodium trimethoxyborohydride results in reductive cyclization.
