A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones

The base-promoted Michael–aldol anionic domino reactions of cyclic α-nitro ketones and α,β-unsaturated aldehydes afforded bicyclo[n.3.1]alkanone systems of seven different ring sizes (n = 3–9), normally in excellent yields. This can be considered the first general method for the synthesis of this ty...

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Detalles Bibliográficos
Autores: Rodriguez, Jean, Giorgi Poletti, Giorgio, Ruiz Serrano, Miriam, López-Alvarado Gutiérrez, María Pilar, Menéndez Ramos, José Carlos
Tipo de recurso: artículo
Fecha de publicación:2011
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/128700
Acceso en línea:https://hdl.handle.net/20.500.14352/128700
Access Level:acceso abierto
Palabra clave:547
Bicyclic compounds
Domino reactions
Michael addition
Aldol reactions
Diastereoselectivity
Química orgánica (Química)
2306.04 Química de Los Compuestos Bicíclicos
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spelling A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐NitrocycloalkanonesRodriguez, JeanGiorgi Poletti, GiorgioRuiz Serrano, MiriamLópez-Alvarado Gutiérrez, María PilarMenéndez Ramos, José Carlos547Bicyclic compoundsDomino reactionsMichael additionAldol reactionsDiastereoselectivityQuímica orgánica (Química)2306.04 Química de Los Compuestos BicíclicosThe base-promoted Michael–aldol anionic domino reactions of cyclic α-nitro ketones and α,β-unsaturated aldehydes afforded bicyclo[n.3.1]alkanone systems of seven different ring sizes (n = 3–9), normally in excellent yields. This can be considered the first general method for the synthesis of this type of carbocycle. Furthermore, up to four stereocentres are generated, three of which are contiguous and include a functionalized quaternary bridgehead carbon atom. The diastereoselectivity was often complete, was much higher than in les general reactions based on related domino processes, and involved the generation of a different major diastereomer due to the control of the Michael and aldol individual steps of the reaction by the nitro groupWileyUniversidad Complutense de Madrid20112011-01-0120112011-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://hdl.handle.net/20.500.14352/128700reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)InglésengMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available CTQ2009-12320-BQUMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available ACI2009- 0956UCM Not available 920234open accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1287002026-06-02T12:44:21Z
dc.title.none.fl_str_mv A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
title A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
spellingShingle A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
Rodriguez, Jean
547
Bicyclic compounds
Domino reactions
Michael addition
Aldol reactions
Diastereoselectivity
Química orgánica (Química)
2306.04 Química de Los Compuestos Bicíclicos
title_short A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
title_full A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
title_fullStr A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
title_full_unstemmed A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
title_sort A General, Diastereoselective Synthesis of Highly Functionalized Bicyclo[<i>n</i>.3.1]alkane Systems Based on an Anionic Domino Reaction of α‐Nitrocycloalkanones
dc.creator.none.fl_str_mv Rodriguez, Jean
Giorgi Poletti, Giorgio
Ruiz Serrano, Miriam
López-Alvarado Gutiérrez, María Pilar
Menéndez Ramos, José Carlos
author Rodriguez, Jean
author_facet Rodriguez, Jean
Giorgi Poletti, Giorgio
Ruiz Serrano, Miriam
López-Alvarado Gutiérrez, María Pilar
Menéndez Ramos, José Carlos
author_role author
author2 Giorgi Poletti, Giorgio
Ruiz Serrano, Miriam
López-Alvarado Gutiérrez, María Pilar
Menéndez Ramos, José Carlos
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Bicyclic compounds
Domino reactions
Michael addition
Aldol reactions
Diastereoselectivity
Química orgánica (Química)
2306.04 Química de Los Compuestos Bicíclicos
topic 547
Bicyclic compounds
Domino reactions
Michael addition
Aldol reactions
Diastereoselectivity
Química orgánica (Química)
2306.04 Química de Los Compuestos Bicíclicos
description The base-promoted Michael–aldol anionic domino reactions of cyclic α-nitro ketones and α,β-unsaturated aldehydes afforded bicyclo[n.3.1]alkanone systems of seven different ring sizes (n = 3–9), normally in excellent yields. This can be considered the first general method for the synthesis of this type of carbocycle. Furthermore, up to four stereocentres are generated, three of which are contiguous and include a functionalized quaternary bridgehead carbon atom. The diastereoselectivity was often complete, was much higher than in les general reactions based on related domino processes, and involved the generation of a different major diastereomer due to the control of the Michael and aldol individual steps of the reaction by the nitro group
publishDate 2011
dc.date.none.fl_str_mv 2011
2011-01-01
2011
2011-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/128700
url https://hdl.handle.net/20.500.14352/128700
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available CTQ2009-12320-BQU
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available ACI2009- 0956
UCM Not available 920234
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
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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
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score 15,811543

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