A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst

Autores
Kim, Hyejin; Gerosa, Gabriela Guillermina; Aronow, Jonas; Kasaplar, Pinar; Ouyang, Jie; Lingnau, Julia B.; Guerry, Paul; Farès, Christophe; List, Benjamin
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
When developing a synthetic methodology, chemists generally optimize a single substrate and then explore the substrate scope of their method. This approach has led to innumerable and widely-used chemical reactions. However, it frequently provides methods that only work on model substrate-like compounds. Perhaps worse, reaction conditions that would enable the conversion of other substrates may be missed. We now show that a different approach, originally proposed by Kagan, in which a collection of structurally distinct substrates are evaluated in a single reaction vessel, can not only provide information on the substrate scope at a much earlier stage in methodology development, but even lead to a broadly applicable synthetic methodology. Using this multi-substrate screening approach, we have identified an efficient and stereoselective imidodiphosphorimidate organocatalyst for scalable Diels?Alder reactions of cyclopentadiene with different classes of α,β-unsaturated aldehydes.
Fil: Kim, Hyejin. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Gerosa, Gabriela Guillermina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Aronow, Jonas. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Kasaplar, Pinar. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Ouyang, Jie. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Lingnau, Julia B.. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Guerry, Paul. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Farès, Christophe. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: List, Benjamin. Max-Planck-Institut für Kohlenforschung; Alemania
Materia
ORGANOCATALYSIS
ASYMMETRIC SYNTHESIS
COMBINATORIAL LIBRARIES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/104577
Acceder
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network_name_str CONICET Digital (CONICET)
spelling A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalystKim, HyejinGerosa, Gabriela GuillerminaAronow, JonasKasaplar, PinarOuyang, JieLingnau, Julia B.Guerry, PaulFarès, ChristopheList, BenjaminORGANOCATALYSISASYMMETRIC SYNTHESISCOMBINATORIAL LIBRARIEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1When developing a synthetic methodology, chemists generally optimize a single substrate and then explore the substrate scope of their method. This approach has led to innumerable and widely-used chemical reactions. However, it frequently provides methods that only work on model substrate-like compounds. Perhaps worse, reaction conditions that would enable the conversion of other substrates may be missed. We now show that a different approach, originally proposed by Kagan, in which a collection of structurally distinct substrates are evaluated in a single reaction vessel, can not only provide information on the substrate scope at a much earlier stage in methodology development, but even lead to a broadly applicable synthetic methodology. Using this multi-substrate screening approach, we have identified an efficient and stereoselective imidodiphosphorimidate organocatalyst for scalable Diels?Alder reactions of cyclopentadiene with different classes of α,β-unsaturated aldehydes.Fil: Kim, Hyejin. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: Gerosa, Gabriela Guillermina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Aronow, Jonas. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: Kasaplar, Pinar. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: Ouyang, Jie. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: Lingnau, Julia B.. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: Guerry, Paul. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: Farès, Christophe. Max-Planck-Institut für Kohlenforschung; AlemaniaFil: List, Benjamin. Max-Planck-Institut für Kohlenforschung; AlemaniaNature Publishing Group2019-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/104577Kim, Hyejin; Gerosa, Gabriela Guillermina; Aronow, Jonas; Kasaplar, Pinar; Ouyang, Jie; et al.; A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst; Nature Publishing Group; Nature Communications; 10; 1; 2-2019; 1-62041-17232041-1723CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.nature.com/articles/s41467-019-08374-zinfo:eu-repo/semantics/altIdentifier/doi/10.1038/s41467-019-08374-zinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:49:46Zoai:ri.conicet.gov.ar:11336/104577instacron: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 09:49:47.215CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
title A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
spellingShingle A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
Kim, Hyejin
ORGANOCATALYSIS
ASYMMETRIC SYNTHESIS
COMBINATORIAL LIBRARIES
title_short A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
title_full A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
title_fullStr A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
title_full_unstemmed A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
title_sort A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst
dc.creator.none.fl_str_mv Kim, Hyejin
Gerosa, Gabriela Guillermina
Aronow, Jonas
Kasaplar, Pinar
Ouyang, Jie
Lingnau, Julia B.
Guerry, Paul
Farès, Christophe
List, Benjamin
author Kim, Hyejin
author_facet Kim, Hyejin
Gerosa, Gabriela Guillermina
Aronow, Jonas
Kasaplar, Pinar
Ouyang, Jie
Lingnau, Julia B.
Guerry, Paul
Farès, Christophe
List, Benjamin
author_role author
author2 Gerosa, Gabriela Guillermina
Aronow, Jonas
Kasaplar, Pinar
Ouyang, Jie
Lingnau, Julia B.
Guerry, Paul
Farès, Christophe
List, Benjamin
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ORGANOCATALYSIS
ASYMMETRIC SYNTHESIS
COMBINATORIAL LIBRARIES
topic ORGANOCATALYSIS
ASYMMETRIC SYNTHESIS
COMBINATORIAL LIBRARIES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv When developing a synthetic methodology, chemists generally optimize a single substrate and then explore the substrate scope of their method. This approach has led to innumerable and widely-used chemical reactions. However, it frequently provides methods that only work on model substrate-like compounds. Perhaps worse, reaction conditions that would enable the conversion of other substrates may be missed. We now show that a different approach, originally proposed by Kagan, in which a collection of structurally distinct substrates are evaluated in a single reaction vessel, can not only provide information on the substrate scope at a much earlier stage in methodology development, but even lead to a broadly applicable synthetic methodology. Using this multi-substrate screening approach, we have identified an efficient and stereoselective imidodiphosphorimidate organocatalyst for scalable Diels?Alder reactions of cyclopentadiene with different classes of α,β-unsaturated aldehydes.
Fil: Kim, Hyejin. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Gerosa, Gabriela Guillermina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Aronow, Jonas. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Kasaplar, Pinar. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Ouyang, Jie. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Lingnau, Julia B.. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Guerry, Paul. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: Farès, Christophe. Max-Planck-Institut für Kohlenforschung; Alemania
Fil: List, Benjamin. Max-Planck-Institut für Kohlenforschung; Alemania
description When developing a synthetic methodology, chemists generally optimize a single substrate and then explore the substrate scope of their method. This approach has led to innumerable and widely-used chemical reactions. However, it frequently provides methods that only work on model substrate-like compounds. Perhaps worse, reaction conditions that would enable the conversion of other substrates may be missed. We now show that a different approach, originally proposed by Kagan, in which a collection of structurally distinct substrates are evaluated in a single reaction vessel, can not only provide information on the substrate scope at a much earlier stage in methodology development, but even lead to a broadly applicable synthetic methodology. Using this multi-substrate screening approach, we have identified an efficient and stereoselective imidodiphosphorimidate organocatalyst for scalable Diels?Alder reactions of cyclopentadiene with different classes of α,β-unsaturated aldehydes.
publishDate 2019
dc.date.none.fl_str_mv 2019-02
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/11336/104577
Kim, Hyejin; Gerosa, Gabriela Guillermina; Aronow, Jonas; Kasaplar, Pinar; Ouyang, Jie; et al.; A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst; Nature Publishing Group; Nature Communications; 10; 1; 2-2019; 1-6
2041-1723
2041-1723
CONICET Digital
CONICET
url http://hdl.handle.net/11336/104577
identifier_str_mv Kim, Hyejin; Gerosa, Gabriela Guillermina; Aronow, Jonas; Kasaplar, Pinar; Ouyang, Jie; et al.; A multi-substrate screening approach for the identification of a broadly applicable Diels-Alder catalyst; Nature Publishing Group; Nature Communications; 10; 1; 2-2019; 1-6
2041-1723
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.nature.com/articles/s41467-019-08374-z
info:eu-repo/semantics/altIdentifier/doi/10.1038/s41467-019-08374-z
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Nature Publishing Group
publisher.none.fl_str_mv Nature Publishing Group
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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