Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols

(Matrix presented) Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted c...

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Detalles Bibliográficos
Autores principales: Duran, F., Leman, L., Ghini, A., Burton, G., Dauban, P., Dodd, R.H.
Formato: JOUR
Materias:
alcohol derivative
amine
aziridine derivative
biological factor
copper
sulfamic acid
sulfonic acid derivative
article
catalysis
chemistry
cyclization
methodology
synthesis
Alcohols
Amines
Aziridines
Biological Factors
Catalysis
Chemistry, Pharmaceutical
Copper
Cyclization
Sulfonic Acids
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_15237060_v4_n15_p2481_Duran
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:(Matrix presented) Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted cyclic sulfamates, which in turn reacted, after nitrogen activation, with a second nucleophile at the carbon atom bearing the oxygen atom. Concomitant removal of the sulfonyloxy moiety thus gave access to polysubstituted amines.

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