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dc.contributor.author
Gerosa, Gabriela Guillermina
dc.contributor.author
Spanevello, Rolando Angel
dc.contributor.author
Suarez, Alejandra Graciela
dc.contributor.author
Sarotti, Ariel Marcelo
dc.date.available
2016-06-09T19:21:39Z
dc.date.issued
2015-08
dc.identifier.citation
Gerosa, Gabriela Guillermina; Spanevello, Rolando Angel; Suarez, Alejandra Graciela; Sarotti, Ariel Marcelo; A joint experimental, in silico and NMR studies towards the rational design of iminium-based organocatalyst derived from renewable sources; American Chemical Society; Journal Of Organic Chemistry; 80; 15; 8-2015; 7626-7634
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/6132
dc.description.abstract
An efficient organocatalyst for iminium-ionbased asymmetric Diels−Alder (DA) reactions has beenrationally designed. The most influential structure−activityrelationships were determined experimentally, while DFTcalculations and NMR studies provided further mechanisticinsight. This knowledge guided an in silico screening of 62different catalysts using an ONIOM(B3LYP/6-31G*:AM1)transition-state modeling, which showed good correlationbetween theory and experiment. The top-scored compoundwas easily synthesized from levoglucosenone, a biomass-derived chiral enone, and evaluated in the DA reaction between (E)-cinnamaldehyde and cyclopentadiene. In line with the computational finding, excellent results (up to 97% ee) were obtained. Inaddition, the catalyst could be easily recovered and reused with no loss in its catalytic activity.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Biomasa
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Rmn
dc.subject
Organocatalizador
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
A joint experimental, in silico and NMR studies towards the rational design of iminium-based organocatalyst derived from renewable sources
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2016-06-08T17:58:43Z
dc.journal.volume
80
dc.journal.number
15
dc.journal.pagination
7626-7634
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington
dc.description.fil
Fil: Gerosa, Gabriela Guillermina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
dc.journal.title
Journal Of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b01214
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.5b01214
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/acs.joc.5b01214
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