Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element

Chiral gold(I) catalysts have been designed based on a modi-fied JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cycliza-tions of 1,6-enynes. These chiral mononuclear catalysts h...

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Autores: Zuccarello, Giuseppe, Mayans, Joan G., Escofet, Imma, Scharnagel, Dagmar, Kirillova, Mariia S., Pérez-Jimeno, Alba H., Calleja, Pilar, Boothe, Jordan R., Echavarren, Antonio M.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
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:2072/522470
Acceso en línea:http://hdl.handle.net/2072/522470
https://doi.org/10.1021/jacs.9b06326
Access Level:acceso abierto
Palabra clave:54
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spelling Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral ElementZuccarello, GiuseppeMayans, Joan G.Escofet, ImmaScharnagel, DagmarKirillova, Mariia S.Pérez-Jimeno, Alba H.Calleja, PilarBoothe, Jordan R.Echavarren, Antonio M.54Chiral gold(I) catalysts have been designed based on a modi-fied JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cycliza-tions of 1,6-enynes. These chiral mononuclear catalysts have been applied for the enantioselective 5-exo-dig and 6-endo-dig cyclization of different 1,6-enynes as well as in the first enan-tioselective total synthesis of three members of the carexane family of natural products. Opposite enantioselectivities have been achieved in seemingly analogous reactions of 1,6-enynes, which result from different chiral folding of the substrates based on attractive aryl-aryl interactions.2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion11858 p.application/vnd.openxmlformats-officedocument.wordprocessingml.documenthttp://hdl.handle.net/2072/522470https://doi.org/10.1021/jacs.9b06326RECERCAT (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)InglésUE (CTQ2016-75960-P)AGAUR (2014 SGR 818)You have selected the Attribution-NonCommercial-NoDerivatives 4.0 International License. This license is permanently located at http://creativecommons.org/licenses/by-nc-nd/4.0/.info:eu-repo/semantics/openAccessoai:recercat.cat:2072/5224702026-05-29T05:05:01Z
dc.title.none.fl_str_mv Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
title Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
spellingShingle Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
Zuccarello, Giuseppe
54
title_short Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
title_full Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
title_fullStr Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
title_full_unstemmed Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
title_sort Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
dc.creator.none.fl_str_mv Zuccarello, Giuseppe
Mayans, Joan G.
Escofet, Imma
Scharnagel, Dagmar
Kirillova, Mariia S.
Pérez-Jimeno, Alba H.
Calleja, Pilar
Boothe, Jordan R.
Echavarren, Antonio M.
author Zuccarello, Giuseppe
author_facet Zuccarello, Giuseppe
Mayans, Joan G.
Escofet, Imma
Scharnagel, Dagmar
Kirillova, Mariia S.
Pérez-Jimeno, Alba H.
Calleja, Pilar
Boothe, Jordan R.
Echavarren, Antonio M.
author_role author
author2 Mayans, Joan G.
Escofet, Imma
Scharnagel, Dagmar
Kirillova, Mariia S.
Pérez-Jimeno, Alba H.
Calleja, Pilar
Boothe, Jordan R.
Echavarren, Antonio M.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 54
topic 54
description Chiral gold(I) catalysts have been designed based on a modi-fied JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cycliza-tions of 1,6-enynes. These chiral mononuclear catalysts have been applied for the enantioselective 5-exo-dig and 6-endo-dig cyclization of different 1,6-enynes as well as in the first enan-tioselective total synthesis of three members of the carexane family of natural products. Opposite enantioselectivities have been achieved in seemingly analogous reactions of 1,6-enynes, which result from different chiral folding of the substrates based on attractive aryl-aryl interactions.
publishDate 2017
dc.date.none.fl_str_mv 2017
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/2072/522470
https://doi.org/10.1021/jacs.9b06326
url http://hdl.handle.net/2072/522470
https://doi.org/10.1021/jacs.9b06326
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv UE (CTQ2016-75960-P)
AGAUR (2014 SGR 818)
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11858 p.
application/vnd.openxmlformats-officedocument.wordprocessingml.document
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
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