Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respec...

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Autores: Fernández Wang, Martí, Parera Briansó, Magda, Parella Coll, Teodor, Lledó Ponsati, Agustí, Le Bras, Jean, Muzart, Jacques, Pla i Quintana, Anna, Roglans i Ribas, Anna
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/13146
Acceso en línea:http://hdl.handle.net/10256/13146
Access Level:acceso abierto
Palabra clave:Reaccions d'addició
Addition reactions
Catàlisi
Catalysis
Catalitzadors de rodi
Rhodium catalyst
Rodi
Rhodium
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spelling Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene ScaffoldsFernández Wang, MartíParera Briansó, MagdaParella Coll, TeodorLledó Ponsati, AgustíLe Bras, JeanMuzart, JacquesPla i Quintana, AnnaRoglans i Ribas, AnnaReaccions d'addicióAddition reactionsCatàlisiCatalysisCatalitzadors de rodiRhodium catalystRodiRhodiumA rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yieldsFinancial support from the Spanish Ministry of Education and Science (MINECO) (Projects No.: CTQ2014-54306-P, CTQ2012-32436 and a RyC contract to A. L.) and the DIUE of the Generalitat de Catalunya (Project No.: 2014SGR931) are acknowledgedWileyMinisterio de Economía y Competitividad (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionpeer-reviewedapplication/pdfhttp://hdl.handle.net/10256/13146http://hdl.handle.net/10256/13146© Advanced Synthesis and Catalysis, 2016, vol. 358, núm. 11, p. 1848-1853Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201600039info:eu-repo/semantics/altIdentifier/issn/1615-4150info:eu-repo/semantics/altIdentifier/eissn/1615-4169info:eu-repo/grantAgreement/MINECO//CTQ2014-54306-PAGAUR/2014-2016/2014 SGR-931Tots els drets reservatsinfo:eu-repo/semantics/openAccessoai:recercat.cat:10256/131462026-05-29T05:05:01Z
dc.title.none.fl_str_mv Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
title Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
spellingShingle Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
Fernández Wang, Martí
Reaccions d'addició
Addition reactions
Catàlisi
Catalysis
Catalitzadors de rodi
Rhodium catalyst
Rodi
Rhodium
title_short Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
title_full Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
title_fullStr Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
title_full_unstemmed Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
title_sort Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
dc.creator.none.fl_str_mv Fernández Wang, Martí
Parera Briansó, Magda
Parella Coll, Teodor
Lledó Ponsati, Agustí
Le Bras, Jean
Muzart, Jacques
Pla i Quintana, Anna
Roglans i Ribas, Anna
author Fernández Wang, Martí
author_facet Fernández Wang, Martí
Parera Briansó, Magda
Parella Coll, Teodor
Lledó Ponsati, Agustí
Le Bras, Jean
Muzart, Jacques
Pla i Quintana, Anna
Roglans i Ribas, Anna
author_role author
author2 Parera Briansó, Magda
Parella Coll, Teodor
Lledó Ponsati, Agustí
Le Bras, Jean
Muzart, Jacques
Pla i Quintana, Anna
Roglans i Ribas, Anna
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Reaccions d'addició
Addition reactions
Catàlisi
Catalysis
Catalitzadors de rodi
Rhodium catalyst
Rodi
Rhodium
topic Reaccions d'addició
Addition reactions
Catàlisi
Catalysis
Catalitzadors de rodi
Rhodium catalyst
Rodi
Rhodium
description A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields
publishDate 2016
dc.date.none.fl_str_mv 2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
peer-reviewed
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/13146
http://hdl.handle.net/10256/13146
url http://hdl.handle.net/10256/13146
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201600039
info:eu-repo/semantics/altIdentifier/issn/1615-4150
info:eu-repo/semantics/altIdentifier/eissn/1615-4169
info:eu-repo/grantAgreement/MINECO//CTQ2014-54306-P
AGAUR/2014-2016/2014 SGR-931
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv © Advanced Synthesis and Catalysis, 2016, vol. 358, núm. 11, p. 1848-1853
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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