1644530-98-2Relevant academic research and scientific papers
Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes
Ciesielski, Jennifer,Dequirez, Geoffroy,Retailleau, Pascal,Gandon, Vincent,Dauban, Philippe
, p. 9338 - 9347 (2016)
The RhII-catalyzed oxyamination and diamination of alkenes generate 1,2-amino alcohols and 1,2-diamines, respectively, in good to excellent yields and with complete regiocontrol. In the case of diamination, the intramolecular reaction provides
Catalytic intermolecular alkene oxyamination with nitrenes
Dequirez, Geoffroy,Ciesielski, Jennifer,Retailleau, Pascal,Dauban, Philippe
supporting information, p. 8929 - 8933 (2014/07/22)
The RhII-catalyzed intermolecular addition of nitrenes to aromatic and aliphatic alkenes provides vicinal amino alcohols with yields of up to 95 % and complete regioselectivity. This 1,2-oxyamination reaction involves the formation of an aziridine intermediate that undergoes in situ ring opening. The latter is induced by the Rh-bound nitrene that behaves as a Lewis acid. Rhodium drive: The RhII-catalyzed intermolecular addition of nitrenes to alkenes allows the formation of vicinal amino alcohols with complete regioselectivity. The oxyamination reaction occurs with yields of up to 95 %. The mechanism involves the formation of an aziridine intermediate that undergoes a nucleophilic ring opening after activation by the Lewis acidic rhodium-bound nitrene (see scheme; esp=α,α,α',α'-tetramethyl-1,3- benzenedipropionate, Tces=trichloraethylsulfamyl).
