Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes

Light excitation of ortho-alkyl aromatic ketones and aldehydes enables access to hydroxy-o-quinodimethanes. These reactive electron-rich intermediates are sufficiently long-lived to productively engage in chemical processes, mainly acting as dienes in [4+2]-cycloadditions with electron-poor alkenes....

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Detalles Bibliográficos
Autores: Cuadros, Sara, Melchiorre, Paolo
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/335531
Acceso en línea:http://hdl.handle.net/2072/335531
https://doi.org/10.1002/ejoc.201800081
Access Level:acceso abierto
Palabra clave:54
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spelling Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanesCuadros, SaraMelchiorre, Paolo54Light excitation of ortho-alkyl aromatic ketones and aldehydes enables access to hydroxy-o-quinodimethanes. These reactive electron-rich intermediates are sufficiently long-lived to productively engage in chemical processes, mainly acting as dienes in [4+2]-cycloadditions with electron-poor alkenes. Since the early discovery of this photoenolization mechanism, which dates back to 1961, a variety of transformations has been developed, providing a photochemical alternative to classical Diels-Alder chemistry. However, enantioselective catalytic versions of the photenoliza tion/Diels-Alder sequence have remained elusive until recently. This review describes how the field of enantioselective organocatalysis has provided suitable tools to stereoselectively trap photochemically generated hydroxy-o-quinodimethanes. Recent studies also demonstrated that the chemistry is not limited to cycloaddition-type manifolds, but it can be expanded to develop intermolecular enantioselective addition processes.2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion2884 p.application/pdfhttp://hdl.handle.net/2072/335531https://doi.org/10.1002/ejoc.201800081RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/grantAgreement/EC/FP7/681840L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2072/3355312026-05-29T05:05:01Z
dc.title.none.fl_str_mv Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
title Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
spellingShingle Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
Cuadros, Sara
54
title_short Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
title_full Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
title_fullStr Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
title_full_unstemmed Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
title_sort Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
dc.creator.none.fl_str_mv Cuadros, Sara
Melchiorre, Paolo
author Cuadros, Sara
author_facet Cuadros, Sara
Melchiorre, Paolo
author_role author
author2 Melchiorre, Paolo
author2_role author
dc.subject.none.fl_str_mv 54
topic 54
description Light excitation of ortho-alkyl aromatic ketones and aldehydes enables access to hydroxy-o-quinodimethanes. These reactive electron-rich intermediates are sufficiently long-lived to productively engage in chemical processes, mainly acting as dienes in [4+2]-cycloadditions with electron-poor alkenes. Since the early discovery of this photoenolization mechanism, which dates back to 1961, a variety of transformations has been developed, providing a photochemical alternative to classical Diels-Alder chemistry. However, enantioselective catalytic versions of the photenoliza tion/Diels-Alder sequence have remained elusive until recently. This review describes how the field of enantioselective organocatalysis has provided suitable tools to stereoselectively trap photochemically generated hydroxy-o-quinodimethanes. Recent studies also demonstrated that the chemistry is not limited to cycloaddition-type manifolds, but it can be expanded to develop intermolecular enantioselective addition processes.
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/335531
https://doi.org/10.1002/ejoc.201800081
url http://hdl.handle.net/2072/335531
https://doi.org/10.1002/ejoc.201800081
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/EC/FP7/681840
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 2884 p.
application/pdf
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reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
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