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Abstract:

(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.

Registro:

Documento: Artículo
Título:Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
Autor:Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R.H.
Filiación:Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
Institut de Chimie des Substances Naturelles, C. N. R. S., F-91198 Gif-sur-Yvette, France
Palabras clave: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
Año:2002
Volumen:4
Número:15
Página de inicio:2481
Página de fin:2483
DOI: http://dx.doi.org/10.1021/ol0200899
Título revista:Organic Letters
Título revista abreviado:Org. Lett.
ISSN:15237060
CAS:Alcohols; Amines; Aziridines; Biological Factors; Copper, 7440-50-8; sulfamic acid, 5329-14-6; Sulfonic Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v4_n15_p2481_Duran

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Citas:

---------- APA ----------
Duran, F., Leman, L., Ghini, A., Burton, G., Dauban, P. & Dodd, R.H. (2002) . Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols. Organic Letters, 4(15), 2481-2483.
http://dx.doi.org/10.1021/ol0200899
---------- CHICAGO ----------
Duran, F., Leman, L., Ghini, A., Burton, G., Dauban, P., Dodd, R.H. "Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols" . Organic Letters 4, no. 15 (2002) : 2481-2483.
http://dx.doi.org/10.1021/ol0200899
---------- MLA ----------
Duran, F., Leman, L., Ghini, A., Burton, G., Dauban, P., Dodd, R.H. "Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols" . Organic Letters, vol. 4, no. 15, 2002, pp. 2481-2483.
http://dx.doi.org/10.1021/ol0200899
---------- VANCOUVER ----------
Duran, F., Leman, L., Ghini, A., Burton, G., Dauban, P., Dodd, R.H. Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols. Org. Lett. 2002;4(15):2481-2483.
http://dx.doi.org/10.1021/ol0200899