Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene

Autores
Gandolfi Donadío, Lucía; Galetti, Mariana Alejandra; Giorgi, Gianluca; Rasparini, Marcello; Comin, Maria Julieta
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the anti adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the syn adduct as major isomer.
Fil: Gandolfi Donadío, Lucía. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; Argentina
Fil: Galetti, Mariana Alejandra. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; Argentina
Fil: Giorgi, Gianluca. Università degli Studi di Siena; Italia
Fil: Rasparini, Marcello. Chemessentia SRL; Italia
Fil: Comin, Maria Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; Argentina
Materia
Michael Addition
Phenylacetheldehyde
Organocatalyst
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:11336/53729
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and NitrostyreneGandolfi Donadío, LucíaGaletti, Mariana AlejandraGiorgi, GianlucaRasparini, MarcelloComin, Maria JulietaMichael AdditionPhenylacetheldehydeOrganocatalysthttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the anti adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the syn adduct as major isomer.Fil: Gandolfi Donadío, Lucía. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; ArgentinaFil: Galetti, Mariana Alejandra. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; ArgentinaFil: Giorgi, Gianluca. Università degli Studi di Siena; ItaliaFil: Rasparini, Marcello. Chemessentia SRL; ItaliaFil: Comin, Maria Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; ArgentinaAmerican Chemical Society2016-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/53729Gandolfi Donadío, Lucía; Galetti, Mariana Alejandra; Giorgi, Gianluca; Rasparini, Marcello; Comin, Maria Julieta; Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene; American Chemical Society; Journal of Organic Chemistry; 81; 17; 9-2016; 7952-79570022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.6b01061info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b01061info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:00Zoai:ri.conicet.gov.ar:11336/53729instacron: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 09:40:00.462CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
title Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
spellingShingle Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
Gandolfi Donadío, Lucía
Michael Addition
Phenylacetheldehyde
Organocatalyst
title_short Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
title_full Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
title_fullStr Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
title_full_unstemmed Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
title_sort Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
dc.creator.none.fl_str_mv Gandolfi Donadío, Lucía
Galetti, Mariana Alejandra
Giorgi, Gianluca
Rasparini, Marcello
Comin, Maria Julieta
author Gandolfi Donadío, Lucía
author_facet Gandolfi Donadío, Lucía
Galetti, Mariana Alejandra
Giorgi, Gianluca
Rasparini, Marcello
Comin, Maria Julieta
author_role author
author2 Galetti, Mariana Alejandra
Giorgi, Gianluca
Rasparini, Marcello
Comin, Maria Julieta
author2_role author
author
author
author
dc.subject.none.fl_str_mv Michael Addition
Phenylacetheldehyde
Organocatalyst
topic Michael Addition
Phenylacetheldehyde
Organocatalyst
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the anti adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the syn adduct as major isomer.
Fil: Gandolfi Donadío, Lucía. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; Argentina
Fil: Galetti, Mariana Alejandra. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; Argentina
Fil: Giorgi, Gianluca. Università degli Studi di Siena; Italia
Fil: Rasparini, Marcello. Chemessentia SRL; Italia
Fil: Comin, Maria Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Industrial. Centro de Investigación y Desarrollo en Química; Argentina
description Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the anti adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the syn adduct as major isomer.
publishDate 2016
dc.date.none.fl_str_mv 2016-09
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/11336/53729
Gandolfi Donadío, Lucía; Galetti, Mariana Alejandra; Giorgi, Gianluca; Rasparini, Marcello; Comin, Maria Julieta; Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene; American Chemical Society; Journal of Organic Chemistry; 81; 17; 9-2016; 7952-7957
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/53729
identifier_str_mv Gandolfi Donadío, Lucía; Galetti, Mariana Alejandra; Giorgi, Gianluca; Rasparini, Marcello; Comin, Maria Julieta; Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene; American Chemical Society; Journal of Organic Chemistry; 81; 17; 9-2016; 7952-7957
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.6b01061
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b01061
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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