1283728-65-3Relevant academic research and scientific papers
Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones
Harding, Sarah L.,Savage, G. Paul
, p. 4759 - 4766 (2012/08/08)
N-Aryl 4-methylene-2-oxazolidinones, prepared via the corresponding O-propargyl carbamates, underwent nitrile oxide cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.
Investigations into competitive cycloaddition/cyclization or elimination from 1,1-dimethyl-propargylcarbamates of anilines
Delatouche, Regis,Lesage, Aurelien,Collette, Floraine,Heroguez, Valerie,Bertrand, Philippe
, p. 166 - 173 (2011/10/12)
The copper-catalyzed reaction of 1,1-dimethyl-O-propargyl aniline carbamates was studied and revealed the unexpected formation of oxazolidin-2-ones and alkylamines. An in-depth study of the reaction conditions showed that the formation of these products was highly dependent on the solvent, copper catalyst and aniline substituents. The reaction can be oriented towards oxazolidinones in pyridine and alkylamines in ethanol, whereas cycloaddition can be achieved in dry tetrahydrofuran.
