Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes

N-Heterocyclic carbene (NHC) catalysts are used for the first time to mediate asymmetric [8+2] cycloadditions of enals with tropones. The kinetic [8+2] cis-cycloadducts can be epimerized to their trans analogues by simply using increased amounts of base and longer reaction times. Substituted tropone...

Descripción completa

Detalles Bibliográficos
Autores: Wang, Shoulei, Rodríguez-Escrich, Carles, Fianchini, Mauro, Maseras, Feliu, Pericàs, Miquel A.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
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:2072/374855
Acceso en línea:http://hdl.handle.net/2072/374855
https://doi.org/10.1021/acs.orglett.9b00906
Access Level:acceso abierto
Palabra clave:54
id ES_ee86e826960675e5e76ec95d8a2bd07e
oai_identifier_str oai:recercat.cat:2072/374855
network_acronym_str ES
network_name_str España
repository_id_str
spelling Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic CarbenesWang, ShouleiRodríguez-Escrich, CarlesFianchini, MauroMaseras, FeliuPericàs, Miquel A.54N-Heterocyclic carbene (NHC) catalysts are used for the first time to mediate asymmetric [8+2] cycloadditions of enals with tropones. The kinetic [8+2] cis-cycloadducts can be epimerized to their trans analogues by simply using increased amounts of base and longer reaction times. Substituted tropones are also tolerated, and the cycloaddition products can be derivatized by hydrogenation or methanolysis. The main stereochemical features on the results of DFT calculations.2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion3187 p.application/pdfhttp://hdl.handle.net/2072/374855https://doi.org/10.1021/acs.orglett.9b00906RECERCAT (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)InglésCTQ2015-69136-RCTQ2017-87792-RDEC Generalitat de Ca- talunya (Grant 2014SGR827)L'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:2072/3748552026-05-29T05:05:01Z
dc.title.none.fl_str_mv Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
title Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
spellingShingle Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
Wang, Shoulei
54
title_short Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
title_full Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
title_fullStr Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
title_full_unstemmed Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
title_sort Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
dc.creator.none.fl_str_mv Wang, Shoulei
Rodríguez-Escrich, Carles
Fianchini, Mauro
Maseras, Feliu
Pericàs, Miquel A.
author Wang, Shoulei
author_facet Wang, Shoulei
Rodríguez-Escrich, Carles
Fianchini, Mauro
Maseras, Feliu
Pericàs, Miquel A.
author_role author
author2 Rodríguez-Escrich, Carles
Fianchini, Mauro
Maseras, Feliu
Pericàs, Miquel A.
author2_role author
author
author
author
dc.subject.none.fl_str_mv 54
topic 54
description N-Heterocyclic carbene (NHC) catalysts are used for the first time to mediate asymmetric [8+2] cycloadditions of enals with tropones. The kinetic [8+2] cis-cycloadducts can be epimerized to their trans analogues by simply using increased amounts of base and longer reaction times. Substituted tropones are also tolerated, and the cycloaddition products can be derivatized by hydrogenation or methanolysis. The main stereochemical features on the results of DFT calculations.
publishDate 2019
dc.date.none.fl_str_mv 2019
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/2072/374855
https://doi.org/10.1021/acs.orglett.9b00906
url http://hdl.handle.net/2072/374855
https://doi.org/10.1021/acs.orglett.9b00906
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv CTQ2015-69136-R
CTQ2017-87792-R
DEC Generalitat de Ca- talunya (Grant 2014SGR827)
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 3187 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
_version_ 1869423704042110976
score 15,811543

Similares en LA Referencia