Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines

The generation of quaternary and tertiary stereocenters on C-10 of the pyrroloisoquinoline skeleton through intramolecular Mizoroki-Heck reactions of 2-alkenyl substituted pyrroles and pyrrolidines has been studied. The cyclizations proceeded with moderate to good yields (up to 81%), although with l...

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Authors: Rebolledo Azcargorta, Ane, Coya Díaz de Sarralde, Estibaliz, Barbolla Cuadrado, Iratxe, Lete Expósito, María Esther, Sotomayor Anduiza, María Nuria
Format: article
Publication Date:2016
Country:España
Institution:Universidad del País Vasco
Repository:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/64278
Online Access:http://hdl.handle.net/10810/64278
Access Level:Open access
Keyword:C-C coupling
Heck reaction
palladium
heterocycles
asymmetric synthesis
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spelling Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolinesRebolledo Azcargorta, AneCoya Díaz de Sarralde, EstibalizBarbolla Cuadrado, IratxeLete Expósito, María EstherSotomayor Anduiza, María NuriaC-C couplingHeck reactionpalladiumheterocyclesasymmetric synthesisThe generation of quaternary and tertiary stereocenters on C-10 of the pyrroloisoquinoline skeleton through intramolecular Mizoroki-Heck reactions of 2-alkenyl substituted pyrroles and pyrrolidines has been studied. The cyclizations proceeded with moderate to good yields (up to 81%), although with low enantioselection when chiral phosphanes, such as (R)-BINAP, are used as ligands. However, enantiomerically pure 10-substituted pyrrolo[1,2-b]isoquinolines have been efficiently obtained through a diastereoselective approach using chiral non-racemic pyrrolidines as substrates, generating a tertiary stereocenterMinisterio de Economía y Competitividad (CTQ2013-41229-P), Gobierno Vasco (IT-623-13), Universidad del País Vasco / Euskal Herriko Unibertsitatea UPV/EHU (UFI11/22, PPM12/03)Wiley202420242016info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/64278reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MINECO/CTQ2013-41229-P/https://doi.org/10.1002/ejoc.201600082info:eu-repo/semantics/openAccess© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheimoai:addi.ehu.eus:10810/642782026-06-18T09:23:17Z
dc.title.none.fl_str_mv Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
title Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
spellingShingle Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
Rebolledo Azcargorta, Ane
C-C coupling
Heck reaction
palladium
heterocycles
asymmetric synthesis
title_short Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
title_full Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
title_fullStr Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
title_full_unstemmed Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
title_sort Generation of Tertiary and Quaternary Stereocenters via Palladium-Catalyzed Intramolecular Heck-type Reactions for the Stereocontrolled Synthesis of Pyrrolo[1,2-b]isoquinolines
dc.creator.none.fl_str_mv Rebolledo Azcargorta, Ane
Coya Díaz de Sarralde, Estibaliz
Barbolla Cuadrado, Iratxe
Lete Expósito, María Esther
Sotomayor Anduiza, María Nuria
author Rebolledo Azcargorta, Ane
author_facet Rebolledo Azcargorta, Ane
Coya Díaz de Sarralde, Estibaliz
Barbolla Cuadrado, Iratxe
Lete Expósito, María Esther
Sotomayor Anduiza, María Nuria
author_role author
author2 Coya Díaz de Sarralde, Estibaliz
Barbolla Cuadrado, Iratxe
Lete Expósito, María Esther
Sotomayor Anduiza, María Nuria
author2_role author
author
author
author
dc.subject.none.fl_str_mv C-C coupling
Heck reaction
palladium
heterocycles
asymmetric synthesis
topic C-C coupling
Heck reaction
palladium
heterocycles
asymmetric synthesis
description The generation of quaternary and tertiary stereocenters on C-10 of the pyrroloisoquinoline skeleton through intramolecular Mizoroki-Heck reactions of 2-alkenyl substituted pyrroles and pyrrolidines has been studied. The cyclizations proceeded with moderate to good yields (up to 81%), although with low enantioselection when chiral phosphanes, such as (R)-BINAP, are used as ligands. However, enantiomerically pure 10-substituted pyrrolo[1,2-b]isoquinolines have been efficiently obtained through a diastereoselective approach using chiral non-racemic pyrrolidines as substrates, generating a tertiary stereocenter
publishDate 2016
dc.date.none.fl_str_mv 2016
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/64278
url http://hdl.handle.net/10810/64278
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MINECO/CTQ2013-41229-P/
https://doi.org/10.1002/ejoc.201600082
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
eu_rights_str_mv openAccess
rights_invalid_str_mv © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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
_version_ 1869415882562732032
score 15,301603

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