Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines

Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and...

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Autores: Elías Rodríguez, María del Pilar, Carmona Asenjo, Ana Teresa, Moreno Vargas, Antonio José, Robina Ramírez, Inmaculada
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/145957
Acceso en línea:https://hdl.handle.net/11441/145957
https://doi.org/10.3390/catal12080876
Access Level:acceso abierto
Palabra clave:Allenes
Organocatalysis
Phosphines
Pyrrolidines
[3 + 2]-cycloaddition
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spelling Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-TosyliminesElías Rodríguez, María del PilarCarmona Asenjo, Ana TeresaMoreno Vargas, Antonio JoséRobina Ramírez, InmaculadaAllenesOrganocatalysisPhosphinesPyrrolidines[3 + 2]-cycloadditionIminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate enantiocontrol. The stereochemical outcome of the reaction depends on the substituent at the nitrogen atom and hydroxyl groups, the configuration of the stereogenic centers and the distance between the diphenylphosphine group and the pyrrolidine skeleton of the catalyst. The preparation of both enantiomers of the catalyst allowed the corresponding enantiomeric pyrrolines to be obtained with similar yields, diastereo- and enantioselectivities.Ministerio de Ciencia e Innovación CTQ2016–77270-R, PID2020-116460RB-100Junta de Andalucía FQM-345Multidisciplinary Digital Publishing Institute (MDPI)Química OrgánicaMinisterio de Ciencia e Innovación (MICIN). EspañaJunta de Andalucía2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/145957https://doi.org/10.3390/catal12080876reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésCatalysts, 12 (8).CTQ2016–77270-RPID2020-116460RB-100FQM-345https://doi.org/10.3390/catal12080876info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1459572026-06-17T12:51:07Z
dc.title.none.fl_str_mv Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
title Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
spellingShingle Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
Elías Rodríguez, María del Pilar
Allenes
Organocatalysis
Phosphines
Pyrrolidines
[3 + 2]-cycloaddition
title_short Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
title_full Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
title_fullStr Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
title_full_unstemmed Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
title_sort Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
dc.creator.none.fl_str_mv Elías Rodríguez, María del Pilar
Carmona Asenjo, Ana Teresa
Moreno Vargas, Antonio José
Robina Ramírez, Inmaculada
author Elías Rodríguez, María del Pilar
author_facet Elías Rodríguez, María del Pilar
Carmona Asenjo, Ana Teresa
Moreno Vargas, Antonio José
Robina Ramírez, Inmaculada
author_role author
author2 Carmona Asenjo, Ana Teresa
Moreno Vargas, Antonio José
Robina Ramírez, Inmaculada
author2_role author
author
author
dc.contributor.none.fl_str_mv Química Orgánica
Ministerio de Ciencia e Innovación (MICIN). España
Junta de Andalucía
dc.subject.none.fl_str_mv Allenes
Organocatalysis
Phosphines
Pyrrolidines
[3 + 2]-cycloaddition
topic Allenes
Organocatalysis
Phosphines
Pyrrolidines
[3 + 2]-cycloaddition
description Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate enantiocontrol. The stereochemical outcome of the reaction depends on the substituent at the nitrogen atom and hydroxyl groups, the configuration of the stereogenic centers and the distance between the diphenylphosphine group and the pyrrolidine skeleton of the catalyst. The preparation of both enantiomers of the catalyst allowed the corresponding enantiomeric pyrrolines to be obtained with similar yields, diastereo- and enantioselectivities.
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/145957
https://doi.org/10.3390/catal12080876
url https://hdl.handle.net/11441/145957
https://doi.org/10.3390/catal12080876
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Catalysts, 12 (8).
CTQ2016–77270-R
PID2020-116460RB-100
FQM-345
https://doi.org/10.3390/catal12080876
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.300719

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