Alkynedicobalt complexes in carbohydrates: Synthetic applications

The complexation of alkynes to form dicobalt hexacarbonyl derivatives facilitates the formation, under acid catalysis, of highly stabilized propargylic cations whose reaction with nucleophiles to form propargylic compounds, currently known as the Nicholas reaction, has found ample use in organic syn...

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Detalles Bibliográficos
Autores: Gómez, Ana M., López Pérez, J. Cristóbal
Tipo de recurso: otro
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/233066
Acceso en línea:http://hdl.handle.net/10261/233066
Access Level:acceso abierto
Palabra clave:Alkyne dicobalt
Dicobalt hexacarbonyl
Nicholas reaction
Ferrier rearrangement
Carbohydrates
Glycosylation
Anomerization
Synthesis
Ferrier-Nicholas cations
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spelling Alkynedicobalt complexes in carbohydrates: Synthetic applicationsGómez, Ana M.López Pérez, J. CristóbalAlkyne dicobaltDicobalt hexacarbonylNicholas reactionFerrier rearrangementCarbohydratesGlycosylationAnomerizationSynthesisFerrier-Nicholas cationsThe complexation of alkynes to form dicobalt hexacarbonyl derivatives facilitates the formation, under acid catalysis, of highly stabilized propargylic cations whose reaction with nucleophiles to form propargylic compounds, currently known as the Nicholas reaction, has found ample use in organic synthesis. This transformation has shown to be particularly useful when applied to carbohydrate derivatives. In this chapter, we provide a brief overview on this subject pioneered by early contributions from Isobe’s research group. Thus, carbohydrate-derived dicobalt hexacarbonyl complexes have been used in the epimerization of C-alkynyl glycosides, pyranose ring-opening nucleophile trapping reactions, pyranose ring-opening ring-recyclization leading to medium-sized oxacycles, glycosylation strategies, C-glycosylation, and pyranose to carbocycle transformations, among others. Finally, contributions from our research group focusing on the synthetic applications of Ferrier-Nicholas cations are also presented.We are grateful to the Ministerio de Economia y Competitividad (MINECO, Spain) for financial support (grant CTQ2015-66702-R).ElsevierMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2021202120202021info:eu-repo/semantics/otherhttp://purl.org/coar/resource_type/c_3248Postprintinfo:eu-repo/semantics/acceptedVersioninfo:eu-repo/semantics/bookParthttp://hdl.handle.net/10261/233066reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-66702-Rhttp://dx.doi.org/10.1016/B978-0-12-817467-8.00003-7Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2330662026-05-22T06:33:51Z
dc.title.none.fl_str_mv Alkynedicobalt complexes in carbohydrates: Synthetic applications
title Alkynedicobalt complexes in carbohydrates: Synthetic applications
spellingShingle Alkynedicobalt complexes in carbohydrates: Synthetic applications
Gómez, Ana M.
Alkyne dicobalt
Dicobalt hexacarbonyl
Nicholas reaction
Ferrier rearrangement
Carbohydrates
Glycosylation
Anomerization
Synthesis
Ferrier-Nicholas cations
title_short Alkynedicobalt complexes in carbohydrates: Synthetic applications
title_full Alkynedicobalt complexes in carbohydrates: Synthetic applications
title_fullStr Alkynedicobalt complexes in carbohydrates: Synthetic applications
title_full_unstemmed Alkynedicobalt complexes in carbohydrates: Synthetic applications
title_sort Alkynedicobalt complexes in carbohydrates: Synthetic applications
dc.creator.none.fl_str_mv Gómez, Ana M.
López Pérez, J. Cristóbal
author Gómez, Ana M.
author_facet Gómez, Ana M.
López Pérez, J. Cristóbal
author_role author
author2 López Pérez, J. Cristóbal
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Alkyne dicobalt
Dicobalt hexacarbonyl
Nicholas reaction
Ferrier rearrangement
Carbohydrates
Glycosylation
Anomerization
Synthesis
Ferrier-Nicholas cations
topic Alkyne dicobalt
Dicobalt hexacarbonyl
Nicholas reaction
Ferrier rearrangement
Carbohydrates
Glycosylation
Anomerization
Synthesis
Ferrier-Nicholas cations
description The complexation of alkynes to form dicobalt hexacarbonyl derivatives facilitates the formation, under acid catalysis, of highly stabilized propargylic cations whose reaction with nucleophiles to form propargylic compounds, currently known as the Nicholas reaction, has found ample use in organic synthesis. This transformation has shown to be particularly useful when applied to carbohydrate derivatives. In this chapter, we provide a brief overview on this subject pioneered by early contributions from Isobe’s research group. Thus, carbohydrate-derived dicobalt hexacarbonyl complexes have been used in the epimerization of C-alkynyl glycosides, pyranose ring-opening nucleophile trapping reactions, pyranose ring-opening ring-recyclization leading to medium-sized oxacycles, glycosylation strategies, C-glycosylation, and pyranose to carbocycle transformations, among others. Finally, contributions from our research group focusing on the synthetic applications of Ferrier-Nicholas cations are also presented.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/other
http://purl.org/coar/resource_type/c_3248
Postprint
info:eu-repo/semantics/acceptedVersion
dc.type.openaire.fl_str_mv info:eu-repo/semantics/bookPart
format other
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/233066
url http://hdl.handle.net/10261/233066
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-66702-R
http://dx.doi.org/10.1016/B978-0-12-817467-8.00003-7
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
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