Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde

A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the...

Full description

Autores:
David Rodriguez, Fredy A.
Maldonado Villamil, Mauricio
Guevara Pulido, James
Tipo de recurso:
Article of journal
Fecha de publicación:
2020
Institución:
Universidad El Bosque
Repositorio:
Repositorio U. El Bosque
Idioma:
eng
OAI Identifier:
oai:repositorio.unbosque.edu.co:20.500.12495/3665
Acceso en línea:
http://hdl.handle.net/20.500.12495/3665
https://doi.org/10.1155/2020/9248793
https://repositorio.unbosque.edu.co
Palabra clave:
Reacciones químicas
Catálisis
Enzimas
Rights
openAccess
License
Attribution 4.0 International
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dc.title.spa.fl_str_mv Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
dc.title.translated.spa.fl_str_mv Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
title Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
spellingShingle Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
Reacciones químicas
Catálisis
Enzimas
title_short Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
title_full Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
title_fullStr Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
title_full_unstemmed Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
title_sort Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
dc.creator.fl_str_mv David Rodriguez, Fredy A.
Maldonado Villamil, Mauricio
Guevara Pulido, James
dc.contributor.author.none.fl_str_mv David Rodriguez, Fredy A.
Maldonado Villamil, Mauricio
Guevara Pulido, James
dc.contributor.orcid.none.fl_str_mv Guevara Pulido, James [0000-0001-9134-3719]
dc.subject.decs.spa.fl_str_mv Reacciones químicas
Catálisis
Enzimas
topic Reacciones químicas
Catálisis
Enzimas
description A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction.
publishDate 2020
dc.date.accessioned.none.fl_str_mv 2020-08-04T17:29:06Z
dc.date.available.none.fl_str_mv 2020-08-04T17:29:06Z
dc.date.issued.none.fl_str_mv 2020
dc.type.coar.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.local.none.fl_str_mv Artículo de revista
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dc.type.driver.none.fl_str_mv info:eu-repo/semantics/article
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dc.identifier.issn.none.fl_str_mv 2090-9071
dc.identifier.uri.none.fl_str_mv http://hdl.handle.net/20.500.12495/3665
dc.identifier.doi.none.fl_str_mv https://doi.org/10.1155/2020/9248793
dc.identifier.instname.spa.fl_str_mv instname:Universidad El Bosque
dc.identifier.reponame.spa.fl_str_mv reponame:Repositorio Institucional Universidad El Bosque
dc.identifier.repourl.none.fl_str_mv https://repositorio.unbosque.edu.co
identifier_str_mv 2090-9071
instname:Universidad El Bosque
reponame:Repositorio Institucional Universidad El Bosque
url http://hdl.handle.net/20.500.12495/3665
https://doi.org/10.1155/2020/9248793
https://repositorio.unbosque.edu.co
dc.language.iso.none.fl_str_mv eng
language eng
dc.relation.ispartofseries.spa.fl_str_mv Journal of chemistry, 2090-9071, Vol. 2020
dc.relation.uri.none.fl_str_mv hindawi.com/journals/jchem/2020/9248793/
dc.rights.*.fl_str_mv Attribution 4.0 International
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by/4.0/
dc.rights.local.spa.fl_str_mv Acceso abierto
dc.rights.accessrights.none.fl_str_mv http://purl.org/coar/access_right/c_abf2
info:eu-repo/semantics/openAccess
Acceso abierto
dc.rights.creativecommons.none.fl_str_mv 2020-06-28
rights_invalid_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
Acceso abierto
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2020-06-28
eu_rights_str_mv openAccess
dc.format.mimetype.none.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv Hindawi
dc.publisher.journal.spa.fl_str_mv Journal of chemistry
institution Universidad El Bosque
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spelling David Rodriguez, Fredy A.Maldonado Villamil, MauricioGuevara Pulido, JamesGuevara Pulido, James [0000-0001-9134-3719]2020-08-04T17:29:06Z2020-08-04T17:29:06Z20202090-9071http://hdl.handle.net/20.500.12495/3665https://doi.org/10.1155/2020/9248793instname:Universidad El Bosquereponame:Repositorio Institucional Universidad El Bosquehttps://repositorio.unbosque.edu.coapplication/pdfengHindawiJournal of chemistryJournal of chemistry, 2090-9071, Vol. 2020hindawi.com/journals/jchem/2020/9248793/Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/Acceso abiertohttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessAcceso abierto2020-06-28Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehydeOrganocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehydeArtículo de revistahttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1info:eu-repo/semantics/articlehttp://purl.org/coar/version/c_970fb48d4fbd8a85Reacciones químicasCatálisisEnzimasA new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction.ORIGINALFredy A. David Rodriguez , Mauricio Maldonado Villamil_2020.pdfFredy A. David Rodriguez , Mauricio Maldonado Villamil_2020.pdfapplication/pdf1410999https://repositorio.unbosque.edu.co/bitstreams/b602ca30-9f47-476b-a7f7-b28fa58a9ecb/download1acbba4072af65d584c501b4e5ce29beMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8908https://repositorio.unbosque.edu.co/bitstreams/d46d790f-369b-430f-9699-11add7871662/download0175ea4a2d4caec4bbcc37e300941108MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://repositorio.unbosque.edu.co/bitstreams/9b7d7ee0-8f64-46cb-8ba1-0ee1c1cfe535/download8a4605be74aa9ea9d79846c1fba20a33MD53THUMBNAILFredy A. David Rodriguez , Mauricio Maldonado Villamil_2020.pdf.jpgFredy A. David Rodriguez , Mauricio Maldonado Villamil_2020.pdf.jpgIM Thumbnailimage/jpeg9289https://repositorio.unbosque.edu.co/bitstreams/3f9843bb-e728-41d0-a47f-790fd39154dd/downloadeca15fd56d56dc35f6f1826dc669947bMD54TEXTFredy A. David Rodriguez , Mauricio Maldonado Villamil_2020.pdf.txtFredy A. 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