INVESTIGADORES
DI CHENNA Pablo Hector
artículos
Título:
Rhodium(II)-Catalyzed Enantioselective Intermolecular Aziridination of Alkenes
Autor/es:
BOQUET, VINCENT; NASRALLAH, ALI; DANA, ALEJANDRO L.; BRUNARD, ERWAN; DI CHENNA, PABLO H.; DURAN, FERNANDO J.; RETAILLEAU, PASCAL; DARSES, BENJAMIN; SIRCOGLOU, MARIE; DAUBAN, PHILIPPE
Revista:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Editorial:
AMER CHEMICAL SOC
Referencias:
Año: 2022
ISSN:
0002-7863
Resumen:
C4-Symmetrical dirhodium(II) tetracarboxylates are highly efficient catalysts for the asymmetric intermolecular aziridination of substituted alkenes with sulfamates. The reaction proceeds with high levels of efficiency and chemoselectivity to afford aziridines with excellent yields of up to 95% and enantiomeric excesses of up to 99%. The scope of the alkene aziridination includes mono-, di-, and trisubstituted olefins as well as the late-stage functionalization of complex substrates. The reaction can be performed on a gram-scale with a catalyst loading of 0.1 mol %. Our DFT study led us to propose a two-spin-state mechanism, involving a triplet Rhnitrene species as key intermediate to drive the stereocontrolled approach and activation of the substrate.
