Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids

The diastereoselective synthesis of cis and trans steroid-fulleropyrrolidines hybrids by reaction of N-metalated azomethine ylides [Cu(II) or Ag(I)] with the appropriate chiral ligand and C60 is described. The experimental findings reveal that the azomethine ylide stabilized by an allylic group cycl...

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Detalles Bibliográficos
Autores: Suarez, Margarita, Ruiz, Alberto, Almagro, Luis, Coro, Julieta, Maroto, Enrique E., Filippone, Salvatore, Molero, Dolores, Martínez-Alvarez, Roberto, Martín León, Nazario
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/18365
Acceso en línea:https://hdl.handle.net/20.500.14352/18365
Access Level:acceso abierto
Palabra clave:547
Química orgánica (Química)
2306 Química Orgánica
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oai_identifier_str oai:docta.ucm.es:20.500.14352/18365
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spelling Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine HybridsSuarez, MargaritaRuiz, AlbertoAlmagro, LuisCoro, JulietaMaroto, Enrique E.Filippone, SalvatoreMolero, DoloresMartínez-Alvarez, RobertoMartín León, Nazario547Química orgánica (Química)2306 Química OrgánicaThe diastereoselective synthesis of cis and trans steroid-fulleropyrrolidines hybrids by reaction of N-metalated azomethine ylides [Cu(II) or Ag(I)] with the appropriate chiral ligand and C60 is described. The experimental findings reveal that the azomethine ylide stabilized by an allylic group cycloadds to [60]fullerene in an efficient manner and with a good diastereomeric excess. Furthermore, the new generated stereocenters are fully controlled by the catalytic systems used without being influenced by the chirality of the steroid. Interestingly, by this synthetic methodology the each one of the four possible stereoisomers have efficiently been obtained and characterized by CD spectra.ACSUniversidad Complutense de Madrid20172017-01-0120172017-01-01journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/18365reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/183652026-06-02T12:44:21Z
dc.title.none.fl_str_mv Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
title Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
spellingShingle Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
Suarez, Margarita
547
Química orgánica (Química)
2306 Química Orgánica
title_short Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
title_full Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
title_fullStr Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
title_full_unstemmed Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
title_sort Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
dc.creator.none.fl_str_mv Suarez, Margarita
Ruiz, Alberto
Almagro, Luis
Coro, Julieta
Maroto, Enrique E.
Filippone, Salvatore
Molero, Dolores
Martínez-Alvarez, Roberto
Martín León, Nazario
author Suarez, Margarita
author_facet Suarez, Margarita
Ruiz, Alberto
Almagro, Luis
Coro, Julieta
Maroto, Enrique E.
Filippone, Salvatore
Molero, Dolores
Martínez-Alvarez, Roberto
Martín León, Nazario
author_role author
author2 Ruiz, Alberto
Almagro, Luis
Coro, Julieta
Maroto, Enrique E.
Filippone, Salvatore
Molero, Dolores
Martínez-Alvarez, Roberto
Martín León, Nazario
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Química orgánica (Química)
2306 Química Orgánica
topic 547
Química orgánica (Química)
2306 Química Orgánica
description The diastereoselective synthesis of cis and trans steroid-fulleropyrrolidines hybrids by reaction of N-metalated azomethine ylides [Cu(II) or Ag(I)] with the appropriate chiral ligand and C60 is described. The experimental findings reveal that the azomethine ylide stabilized by an allylic group cycloadds to [60]fullerene in an efficient manner and with a good diastereomeric excess. Furthermore, the new generated stereocenters are fully controlled by the catalytic systems used without being influenced by the chirality of the steroid. Interestingly, by this synthetic methodology the each one of the four possible stereoisomers have efficiently been obtained and characterized by CD spectra.
publishDate 2017
dc.date.none.fl_str_mv 2017
2017-01-01
2017
2017-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/18365
url https://hdl.handle.net/20.500.14352/18365
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv ACS
publisher.none.fl_str_mv ACS
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869411553183268864
score 15,300724

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