1229643-27-9Relevant academic research and scientific papers
Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions
Chen, Ming,Dong, Guangbin
, p. 14889 - 14897 (2019)
A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible α-deprotonation by a Cu(II)-OtBu species followed by further oxidation of the resulting Cu enolate.
Unusual skeletal rearrangement of unsaturated seven-membered lactams into fused pyrrolidinolactones
Alvarez, Silvia,Dominguez, Gema,Gradillas, Ana,Perez-Castells, Javier
, p. 3094 - 3102 (2013/06/27)
Unsaturated ε-lactams undergo a novel process involving a skeletal reorganization to give fused pyrrolidine-lactones by reaction with aromatic α-bromo ketones in the presence of 1,4-diazabicyclo[2.2.2]octane and a base. The process involves the formation
Nitrogen ylide-mediated cyclopropanation of lactams and lactones
Villar, Irene Suarez del,Gradillas, Ana,Domínguez, Gema,Pérez-Castells, Javier
supporting information; scheme or table, p. 3095 - 3098 (2010/08/07)
Cyclopropanation of α,β-unsaturated δ-lactams and δ-lactones mediated by nitrogen ylides is described. The process tolerates different alkyl halides and gives efficiently bicyclo[4.1.0]heptanes in a totally stereoselective manner. On the other hand, ε-lac
