Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization

The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the desymmetrization of the starting material and leads to the direct formation o...

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Autores: Rodríguez López, Sandra, Uria Pujana, Uxue, Reyes Martín, Efraim, Carrillo Fernández, María Luisa, Tejero, Tomás, Merino, Pedro, Vicario Hernando, José Luis
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/63356
Acceso en línea:http://hdl.handle.net/10810/63356
Access Level:acceso abierto
Palabra clave:alkaloids
asymmetric catalysis
brønsted Acids
desymmetrization
organocatalysis
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spelling Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular DesymmetrizationRodríguez López, SandraUria Pujana, UxueReyes Martín, EfraimCarrillo Fernández, María LuisaTejero, TomásMerino, PedroVicario Hernando, José Luisalkaloidsasymmetric catalysisbrønsted AcidsdesymmetrizationorganocatalysisThe enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the desymmetrization of the starting material and leads to the direct formation of the 8-azabicyclo[3.2.1]octane scaffold with excellent stereoselectivity. The synthetic applicability of the reaction was demonstrated by the enantioselective synthesis of the two natural products (−)-α-tropanol and (+)-ferruginine.Spanish MCIU (FEDER-CTQ2017-83633-P, FEDER-CTQ2016-76155-R and FPU fellowship to S. R.), Basque Government (IT908-16), Government of Aragón (Grupos Consolidados, E.34-17R).Wiley-VCH202320232020info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/63356reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MCIU/CTQ2017-83633-P/info:eu-repo/grantAgreement/MCIU/CTQ2016-76155-R/https://doi.org/10.1002/anie.202000650info:eu-repo/semantics/openAccess© 2020, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheimoai:addi.ehu.eus:10810/633562026-06-18T09:23:17Z
dc.title.none.fl_str_mv Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
title Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
spellingShingle Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
Rodríguez López, Sandra
alkaloids
asymmetric catalysis
brønsted Acids
desymmetrization
organocatalysis
title_short Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
title_full Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
title_fullStr Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
title_full_unstemmed Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
title_sort Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
dc.creator.none.fl_str_mv Rodríguez López, Sandra
Uria Pujana, Uxue
Reyes Martín, Efraim
Carrillo Fernández, María Luisa
Tejero, Tomás
Merino, Pedro
Vicario Hernando, José Luis
author Rodríguez López, Sandra
author_facet Rodríguez López, Sandra
Uria Pujana, Uxue
Reyes Martín, Efraim
Carrillo Fernández, María Luisa
Tejero, Tomás
Merino, Pedro
Vicario Hernando, José Luis
author_role author
author2 Uria Pujana, Uxue
Reyes Martín, Efraim
Carrillo Fernández, María Luisa
Tejero, Tomás
Merino, Pedro
Vicario Hernando, José Luis
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv alkaloids
asymmetric catalysis
brønsted Acids
desymmetrization
organocatalysis
topic alkaloids
asymmetric catalysis
brønsted Acids
desymmetrization
organocatalysis
description The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the desymmetrization of the starting material and leads to the direct formation of the 8-azabicyclo[3.2.1]octane scaffold with excellent stereoselectivity. The synthetic applicability of the reaction was demonstrated by the enantioselective synthesis of the two natural products (−)-α-tropanol and (+)-ferruginine.
publishDate 2020
dc.date.none.fl_str_mv 2020
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/63356
url http://hdl.handle.net/10810/63356
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MCIU/CTQ2017-83633-P/
info:eu-repo/grantAgreement/MCIU/CTQ2016-76155-R/
https://doi.org/10.1002/anie.202000650
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
© 2020, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
eu_rights_str_mv openAccess
rights_invalid_str_mv © 2020, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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