Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone

Autores
Zurita, Mariano; Avila, Aylén; Spanevello, Rolando Angel; Suarez, Alejandra Graciela; Sarotti, Ariel Marcelo
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A short and efficient methodology for the synthesis of chiral dioxa-caged Compounds from levoglucose-none, a biomass-derived enone, is herein Presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.
Fil: Zurita, Mariano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Avila, Aylén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Materia
Montmorillonite K-10
Caged Compounds
Rearrangements
Levoglucosenone
Biomass
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/6131
Acceder
id CONICETDig_32d1d44240552ac2527bfc710ab564ed
oai_identifier_str oai:ri.conicet.gov.ar:11336/6131
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenoneZurita, MarianoAvila, AylénSpanevello, Rolando AngelSuarez, Alejandra GracielaSarotti, Ariel MarceloMontmorillonite K-10Caged CompoundsRearrangementsLevoglucosenoneBiomasshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A short and efficient methodology for the synthesis of chiral dioxa-caged Compounds from levoglucose-none, a biomass-derived enone, is herein Presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.Fil: Zurita, Mariano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Avila, Aylén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaElsevier2015-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6131Zurita, Mariano; Avila, Aylén; Spanevello, Rolando Angel; Suarez, Alejandra Graciela; Sarotti, Ariel Marcelo; Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone; Elsevier; Carbohydrate Research; 402; 1-2015; 67-700008-6215enginfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2014.07.019info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0008621514003036info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:56:04Zoai:ri.conicet.gov.ar:11336/6131instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:56:04.97CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
title Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
spellingShingle Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
Zurita, Mariano
Montmorillonite K-10
Caged Compounds
Rearrangements
Levoglucosenone
Biomass
title_short Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
title_full Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
title_fullStr Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
title_full_unstemmed Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
title_sort Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
dc.creator.none.fl_str_mv Zurita, Mariano
Avila, Aylén
Spanevello, Rolando Angel
Suarez, Alejandra Graciela
Sarotti, Ariel Marcelo
author Zurita, Mariano
author_facet Zurita, Mariano
Avila, Aylén
Spanevello, Rolando Angel
Suarez, Alejandra Graciela
Sarotti, Ariel Marcelo
author_role author
author2 Avila, Aylén
Spanevello, Rolando Angel
Suarez, Alejandra Graciela
Sarotti, Ariel Marcelo
author2_role author
author
author
author
dc.subject.none.fl_str_mv Montmorillonite K-10
Caged Compounds
Rearrangements
Levoglucosenone
Biomass
topic Montmorillonite K-10
Caged Compounds
Rearrangements
Levoglucosenone
Biomass
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A short and efficient methodology for the synthesis of chiral dioxa-caged Compounds from levoglucose-none, a biomass-derived enone, is herein Presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.
Fil: Zurita, Mariano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Avila, Aylén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
description A short and efficient methodology for the synthesis of chiral dioxa-caged Compounds from levoglucose-none, a biomass-derived enone, is herein Presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.
publishDate 2015
dc.date.none.fl_str_mv 2015-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/6131
Zurita, Mariano; Avila, Aylén; Spanevello, Rolando Angel; Suarez, Alejandra Graciela; Sarotti, Ariel Marcelo; Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone; Elsevier; Carbohydrate Research; 402; 1-2015; 67-70
0008-6215
url http://hdl.handle.net/11336/6131
identifier_str_mv Zurita, Mariano; Avila, Aylén; Spanevello, Rolando Angel; Suarez, Alejandra Graciela; Sarotti, Ariel Marcelo; Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone; Elsevier; Carbohydrate Research; 402; 1-2015; 67-70
0008-6215
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2014.07.019
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0008621514003036
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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