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: Duran, Fernando Javier, Leman, Loïc, Ghini, Alberto Antonio, Burton, Gerardo, Dauban, Philippe, Dodd, Robert H.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2002
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/86459
Acceso en línea:http://hdl.handle.net/11336/86459
Access Level:acceso abierto
Palabra clave:AZIRIDINES
CATALISYS
INTRAMOLECULAR
COPPER
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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.