Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins

Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reac...

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Detalhes bibliográficos
Autores: Bonilla, Pablo, Rey, Yannick P., Holden, Catherine M., Melchiorre, Paolo
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Recursos: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:2072/350698
Acesso em linha:http://hdl.handle.net/2072/350698
https://doi.org/10.1002/anie.201808183
Access Level:acceso abierto
Palavra-chave:54
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spelling Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated OlefinsBonilla, PabloRey, Yannick P.Holden, Catherine M.Melchiorre, Paolo54Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reactivity of chiral iminium ions to trigger radical cascade reactions with high enantioselectivity. By combining two sequential radical- based bond-forming events, the method converts unactivated olefins and a,b-unsaturated aldehydes into chiral adducts in a single step. The implementation of an asymmetric three- component radical cascade further demonstrates the complex- ity-generating power of this photochemical strategy.2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion12819 p.application/pdfhttp://hdl.handle.net/2072/350698https://doi.org/10.1002/anie.201808183RECERCAT (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:2072/3506982026-05-29T05:05:01Z
dc.title.none.fl_str_mv Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
title Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
spellingShingle Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
Bonilla, Pablo
54
title_short Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
title_full Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
title_fullStr Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
title_full_unstemmed Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
title_sort Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
dc.creator.none.fl_str_mv Bonilla, Pablo
Rey, Yannick P.
Holden, Catherine M.
Melchiorre, Paolo
author Bonilla, Pablo
author_facet Bonilla, Pablo
Rey, Yannick P.
Holden, Catherine M.
Melchiorre, Paolo
author_role author
author2 Rey, Yannick P.
Holden, Catherine M.
Melchiorre, Paolo
author2_role author
author
author
dc.subject.none.fl_str_mv 54
topic 54
description Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reactivity of chiral iminium ions to trigger radical cascade reactions with high enantioselectivity. By combining two sequential radical- based bond-forming events, the method converts unactivated olefins and a,b-unsaturated aldehydes into chiral adducts in a single step. The implementation of an asymmetric three- component radical cascade further demonstrates the complex- ity-generating power of this photochemical strategy.
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/2072/350698
https://doi.org/10.1002/anie.201808183
url http://hdl.handle.net/2072/350698
https://doi.org/10.1002/anie.201808183
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 12819 p.
application/pdf
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
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
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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