908592-15-4Relevant academic research and scientific papers
New directions for the Morita-Baylis-Hillman reaction; homologous aldol adducts via epoxide opening
Krafft, Marie E.,Wright, James A.
, p. 2977 - 2979 (2008/09/19)
Under trialkylphosphine catalyzed Morita-Baylis-Hillman reaction conditions, epoxides react with enones to give rise to homologous aldol adducts. The Royal Society of Chemistry 2006.
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.
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
