Light-triggered Enantioselective Organocatalytic Mannich-type Reaction

<div> <p> Abstract</p> <p> Disclosed herein is a photochemical organocatalytic strategy for the direct enantioselective Mannich-type reaction of 2-alkyl-benzophenones and cyclic imines. The chemistry exploits the light-triggered enolization of 2-alkyl-benzophenones to generat...

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Autores: Hepburn, Hamish B., Magagnano, Giandomenico, Melchiorre, Paolo
Formato: artículo
Fecha de publicación:2016
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:2072/305755
Acesso em linha:http://hdl.handle.net/2072/305755
https://doi.org/10.1055/s-0036-1588606
Access Level:acceso abierto
Palavra-chave:enantioselective catalysis
organocatalysis
Mannich-type reaction
photochemistry
synthetic methods
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spelling Light-triggered Enantioselective Organocatalytic Mannich-type ReactionHepburn, Hamish B.Magagnano, GiandomenicoMelchiorre, Paoloenantioselective catalysisorganocatalysisMannich-type reactionphotochemistrysynthetic methods<div> <p> Abstract</p> <p> Disclosed herein is a photochemical organocatalytic strategy for the direct enantioselective Mannich-type reaction of 2-alkyl-benzophenones and cyclic imines. The chemistry exploits the light-triggered enolization of 2-alkyl-benzophenones to generate transient hydroxy-<em>o</em>-quinodinomethanes. These fleeting intermediates can be stereoselectively intercepted by imines upon activation with a chiral organic catalyst, derived from natural cinchona alkaloids. The developed method uses mild conditions, simple sources of illumination and easily available substrates and catalysts, affording enantioenriched chiral amines that are difficult to synthesize by other approaches.</p> </div> <p> &nbsp;</p>Thieme E-Journals - Synthesis2016info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/2072/305755https://doi.org/10.1055/s-0036-1588606RECERCAT (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)InglésMinecoAgaurERCMarie CurieSEVERO OCHOA EXCELLENCE ACCREDITATIONChemistry JournalCTQ2013-45938-PSEV-2013-03192014 SGR 1059info:eu-repo/grantAgreement/EC/FP7/ 278541© Georg Thieme Verlag Stuttgart · New Yorkinfo:eu-repo/semantics/openAccessoai:recercat.cat:2072/3057552026-05-29T05:05:01Z
dc.title.none.fl_str_mv Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
title Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
spellingShingle Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
Hepburn, Hamish B.
enantioselective catalysis
organocatalysis
Mannich-type reaction
photochemistry
synthetic methods
title_short Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
title_full Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
title_fullStr Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
title_full_unstemmed Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
title_sort Light-triggered Enantioselective Organocatalytic Mannich-type Reaction
dc.creator.none.fl_str_mv Hepburn, Hamish B.
Magagnano, Giandomenico
Melchiorre, Paolo
author Hepburn, Hamish B.
author_facet Hepburn, Hamish B.
Magagnano, Giandomenico
Melchiorre, Paolo
author_role author
author2 Magagnano, Giandomenico
Melchiorre, Paolo
author2_role author
author
dc.subject.none.fl_str_mv enantioselective catalysis
organocatalysis
Mannich-type reaction
photochemistry
synthetic methods
topic enantioselective catalysis
organocatalysis
Mannich-type reaction
photochemistry
synthetic methods
description <div> <p> Abstract</p> <p> Disclosed herein is a photochemical organocatalytic strategy for the direct enantioselective Mannich-type reaction of 2-alkyl-benzophenones and cyclic imines. The chemistry exploits the light-triggered enolization of 2-alkyl-benzophenones to generate transient hydroxy-<em>o</em>-quinodinomethanes. These fleeting intermediates can be stereoselectively intercepted by imines upon activation with a chiral organic catalyst, derived from natural cinchona alkaloids. The developed method uses mild conditions, simple sources of illumination and easily available substrates and catalysts, affording enantioenriched chiral amines that are difficult to synthesize by other approaches.</p> </div> <p> &nbsp;</p>
publishDate 2016
dc.date.none.fl_str_mv 2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/305755
https://doi.org/10.1055/s-0036-1588606
url http://hdl.handle.net/2072/305755
https://doi.org/10.1055/s-0036-1588606
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Mineco
Agaur
ERC
Marie Curie
SEVERO OCHOA EXCELLENCE ACCREDITATION
Chemistry Journal
CTQ2013-45938-P
SEV-2013-0319
2014 SGR 1059
info:eu-repo/grantAgreement/EC/FP7/ 278541
dc.rights.none.fl_str_mv © Georg Thieme Verlag Stuttgart · New York
info:eu-repo/semantics/openAccess
rights_invalid_str_mv © Georg Thieme Verlag Stuttgart · New York
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Thieme E-Journals - Synthesis
publisher.none.fl_str_mv Thieme E-Journals - Synthesis
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 15.812429

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