Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction

Autores
Ocampo, Romina Andrea; Mandolesi, Sandra Delia; Koll, Liliana Cristina
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1- ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2- trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%). © ARKAT-USA, Inc.
Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Mandolesi, Sandra Delia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Materia
BICYCLIC ALLYLTIN
DIELS-ALDER REACTION
HYDROSTANNATION
HYDROSTANNYLATION
STILLE COUPLING
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/67161
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reactionOcampo, Romina AndreaMandolesi, Sandra DeliaKoll, Liliana CristinaBICYCLIC ALLYLTINDIELS-ALDER REACTIONHYDROSTANNATIONHYDROSTANNYLATIONSTILLE COUPLINGhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1- ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2- trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%). © ARKAT-USA, Inc.Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Mandolesi, Sandra Delia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaArkat2011-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/67161Ocampo, Romina Andrea; Mandolesi, Sandra Delia; Koll, Liliana Cristina; Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction; Arkat; Arkivoc; 2011; 7; 2-2011; 195-2091551-7004CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.717info:eu-repo/semantics/altIdentifier/url/https://quod.lib.umich.edu/a/ark/5550190.0012.717/1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:44:46Zoai:ri.conicet.gov.ar:11336/67161instacron: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:34982025-09-29 10:44:47.17CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
title Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
spellingShingle Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
Ocampo, Romina Andrea
BICYCLIC ALLYLTIN
DIELS-ALDER REACTION
HYDROSTANNATION
HYDROSTANNYLATION
STILLE COUPLING
title_short Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
title_full Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
title_fullStr Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
title_full_unstemmed Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
title_sort Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction
dc.creator.none.fl_str_mv Ocampo, Romina Andrea
Mandolesi, Sandra Delia
Koll, Liliana Cristina
author Ocampo, Romina Andrea
author_facet Ocampo, Romina Andrea
Mandolesi, Sandra Delia
Koll, Liliana Cristina
author_role author
author2 Mandolesi, Sandra Delia
Koll, Liliana Cristina
author2_role author
author
dc.subject.none.fl_str_mv BICYCLIC ALLYLTIN
DIELS-ALDER REACTION
HYDROSTANNATION
HYDROSTANNYLATION
STILLE COUPLING
topic BICYCLIC ALLYLTIN
DIELS-ALDER REACTION
HYDROSTANNATION
HYDROSTANNYLATION
STILLE COUPLING
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1- ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2- trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%). © ARKAT-USA, Inc.
Fil: Ocampo, Romina Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Mandolesi, Sandra Delia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
description In this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1- ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2- trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%). © ARKAT-USA, Inc.
publishDate 2011
dc.date.none.fl_str_mv 2011-02
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/11336/67161
Ocampo, Romina Andrea; Mandolesi, Sandra Delia; Koll, Liliana Cristina; Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction; Arkat; Arkivoc; 2011; 7; 2-2011; 195-209
1551-7004
CONICET Digital
CONICET
url http://hdl.handle.net/11336/67161
identifier_str_mv Ocampo, Romina Andrea; Mandolesi, Sandra Delia; Koll, Liliana Cristina; Bicyclic allyltin derivatives through selective "one pot" hydrostannation - Diels-Alder reaction; Arkat; Arkivoc; 2011; 7; 2-2011; 195-209
1551-7004
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.717
info:eu-repo/semantics/altIdentifier/url/https://quod.lib.umich.edu/a/ark/5550190.0012.717/1
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Arkat
publisher.none.fl_str_mv Arkat
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 13.070432

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