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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Autores principales: Duran, F., Leman, L., Ghini, A., Burton, G., Dauban, P., Dodd, R.H.
Formato: JOUR
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Acceso en línea:http://hdl.handle.net/20.500.12110/paper_15237060_v4_n15_p2481_Duran
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spelling todo:paper_15237060_v4_n15_p2481_Duran2023-10-03T16:20:54Z Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols Duran, F. Leman, L. Ghini, A. Burton, G. Dauban, P. Dodd, R.H. 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 (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. Fil:Duran, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_15237060_v4_n15_p2481_Duran
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 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
spellingShingle 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
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
topic_facet 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
description (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.
format JOUR
author Duran, F.
Leman, L.
Ghini, A.
Burton, G.
Dauban, P.
Dodd, R.H.
author_facet Duran, F.
Leman, L.
Ghini, A.
Burton, G.
Dauban, P.
Dodd, R.H.
author_sort Duran, F.
title Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_short Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_full Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_fullStr Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_full_unstemmed Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_sort intramolecular phl=o mediated copper-catalyzed aziridination of unsaturated sulfamates: a new direct access to polysubstituted amines from simple homoallylic alcohols
url http://hdl.handle.net/20.500.12110/paper_15237060_v4_n15_p2481_Duran
work_keys_str_mv AT duranf intramolecularphlomediatedcoppercatalyzedaziridinationofunsaturatedsulfamatesanewdirectaccesstopolysubstitutedaminesfromsimplehomoallylicalcohols
AT lemanl intramolecularphlomediatedcoppercatalyzedaziridinationofunsaturatedsulfamatesanewdirectaccesstopolysubstitutedaminesfromsimplehomoallylicalcohols
AT ghinia intramolecularphlomediatedcoppercatalyzedaziridinationofunsaturatedsulfamatesanewdirectaccesstopolysubstitutedaminesfromsimplehomoallylicalcohols
AT burtong intramolecularphlomediatedcoppercatalyzedaziridinationofunsaturatedsulfamatesanewdirectaccesstopolysubstitutedaminesfromsimplehomoallylicalcohols
AT daubanp intramolecularphlomediatedcoppercatalyzedaziridinationofunsaturatedsulfamatesanewdirectaccesstopolysubstitutedaminesfromsimplehomoallylicalcohols
AT doddrh intramolecularphlomediatedcoppercatalyzedaziridinationofunsaturatedsulfamatesanewdirectaccesstopolysubstitutedaminesfromsimplehomoallylicalcohols
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