Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction

A bifunctional organocatalytic system consisting of simple pyridine ligands containing separate catalytic functionalities was assembled using ZnCl2. This novel metal-templated catalyst furnished high yields and stereoselectivities towards the aldol reaction. The addition of controlled amounts of wat...

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Detalles Bibliográficos
Autores: Serra-Pont, Anna, Alfonso, Ignacio, Jimeno, Ciril, Solà Oller, Jordi
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2015
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/128325
Acceso en línea:http://hdl.handle.net/10261/128325
Access Level:acceso abierto
Palabra clave:Absorption spectroscopy
Aldol reaction
Asymmetric synthesis
Nuclear magnetic resonance
stereochemistry
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spelling Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reactionSerra-Pont, AnnaAlfonso, IgnacioJimeno, CirilSolà Oller, JordiAbsorption spectroscopyAldol reactionAsymmetric synthesisNuclear magnetic resonanceNuclear magnetic resonancestereochemistryA bifunctional organocatalytic system consisting of simple pyridine ligands containing separate catalytic functionalities was assembled using ZnCl2. This novel metal-templated catalyst furnished high yields and stereoselectivities towards the aldol reaction. The addition of controlled amounts of water turned out to be crucial to dissolve the system and achieve optimal results.Financial support from Mineco (CTQ2012-38594-C02-02 and CTQ2012-38543-C03-03), Generalitat de Catalunya (2014 SGR 231) and EU (FP7-PEOPLE-2012-CIG-321659) is gratefully acknowledged. CJ and JS are Ramón y Cajal fellows (RYC-2010-06750 and RYC-2011-08925). ASP thanks Mineco for a FPI predoctoral fellowship (BES-2013-067087).Peer reviewedRoyal Society of Chemistry (UK)European CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2015info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/128325reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/EC/FP7/321659DOI: 10.1039/c5cc07847d http://pubs.rsc.org/en/content/articlepdf/2015/cc/c5cc07847dSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1283252026-05-22T06:33:51Z
dc.title.none.fl_str_mv Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
title Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
spellingShingle Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
Serra-Pont, Anna
Absorption spectroscopy
Aldol reaction
Asymmetric synthesis
Nuclear magnetic resonance
Nuclear magnetic resonance
stereochemistry
title_short Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
title_full Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
title_fullStr Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
title_full_unstemmed Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
title_sort Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
dc.creator.none.fl_str_mv Serra-Pont, Anna
Alfonso, Ignacio
Jimeno, Ciril
Solà Oller, Jordi
author Serra-Pont, Anna
author_facet Serra-Pont, Anna
Alfonso, Ignacio
Jimeno, Ciril
Solà Oller, Jordi
author_role author
author2 Alfonso, Ignacio
Jimeno, Ciril
Solà Oller, Jordi
author2_role author
author
author
dc.contributor.none.fl_str_mv European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Absorption spectroscopy
Aldol reaction
Asymmetric synthesis
Nuclear magnetic resonance
Nuclear magnetic resonance
stereochemistry
topic Absorption spectroscopy
Aldol reaction
Asymmetric synthesis
Nuclear magnetic resonance
Nuclear magnetic resonance
stereochemistry
description A bifunctional organocatalytic system consisting of simple pyridine ligands containing separate catalytic functionalities was assembled using ZnCl2. This novel metal-templated catalyst furnished high yields and stereoselectivities towards the aldol reaction. The addition of controlled amounts of water turned out to be crucial to dissolve the system and achieve optimal results.
publishDate 2015
dc.date.none.fl_str_mv 2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/128325
url http://hdl.handle.net/10261/128325
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/EC/FP7/321659
DOI: 10.1039/c5cc07847d http://pubs.rsc.org/en/content/articlepdf/2015/cc/c5cc07847d
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Royal Society of Chemistry (UK)
publisher.none.fl_str_mv Royal Society of Chemistry (UK)
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
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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