Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines

An easy and straightforward procedure has been developed for the synthesis of highly enantioenriched pyrrolo-[1,2-a]quinolines through a one-pot process that comprises a domino cyclopropane ring opening/aza-Michael/aldol reaction followed by acid-promoted lactamization. The key feature of the synthe...

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Autores: Sánchez Díez, Eduardo, Vesga, Diana L., Reyes Martín, Efraim, Uria Pujana, Uxue, Carrillo Fernández, María Luisa, Vicario Hernando, José Luis
Tipo de recurso: artículo
Fecha de publicación:2016
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/25991
Acceso en línea:http://hdl.handle.net/10810/25991
Access Level:acceso abierto
Palabra clave:asymetric-synthesis
alpha,beta-unsaturated aldehydes
formylcyclopropane 1,1 diesters
chiral pyrrolizines
aldol reactions
3+2 annulation
silyl ethers
derivatives
cycloaddition
construction
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spelling Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolinesSánchez Díez, EduardoVesga, Diana L.Reyes Martín, EfraimUria Pujana, UxueCarrillo Fernández, María LuisaVicario Hernando, José Luisasymetric-synthesisalpha,beta-unsaturated aldehydesformylcyclopropane 1,1 diesterschiral pyrrolizinesaldol reactions3+2 annulationsilyl ethersderivativescycloadditionconstructionAn easy and straightforward procedure has been developed for the synthesis of highly enantioenriched pyrrolo-[1,2-a]quinolines through a one-pot process that comprises a domino cyclopropane ring opening/aza-Michael/aldol reaction followed by acid-promoted lactamization. The key feature of the synthetic approach relies on the ability of conveniently functionalized cyclopropaneacetaldehydes to undergo organocatalytic activation by a chiral secondary amine that enables the catalytic generation of a donor acceptor cyclopropane. This intermediate has the potential to undergo a ring opening that generates an electrophilic alpha,beta-unsaturated iminium ion that subsequently reacts through the already mentioned domino sequence and in which stereochemical information is very efficiently transferred from the amine catalyst to the final products. Moreover, one of the alkoxycarbonyl moieties can be easily removed by standard hydrolysis/decarboxylation, providing access to the target adducts as single stereoisomers.This research was supported by the Spanish MINECO (FEDER-CTQ2014-52107-P), the Basque Government (Grupos IT328-10), and UPV/EHU (fellowship to E.S. and UFI QOSYC 11/22). Membership in the COST action CM1407 (NatChemDrugs) is also acknowledged.American Chemical Society201820182016info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/25991reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MINECO/FEDER-CTQ2014-52107-P/https://pubs.acs.org/doi/10.1021/acs.orglett.6b00173info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/3.0/es/This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.Atribución-NoComercial-SinDerivadas 3.0 Españaoai:addi.ehu.eus:10810/259912026-06-18T09:23:17Z
dc.title.none.fl_str_mv Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
title Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
spellingShingle Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
Sánchez Díez, Eduardo
asymetric-synthesis
alpha,beta-unsaturated aldehydes
formylcyclopropane 1,1 diesters
chiral pyrrolizines
aldol reactions
3+2 annulation
silyl ethers
derivatives
cycloaddition
construction
title_short Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
title_full Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
title_fullStr Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
title_full_unstemmed Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
title_sort Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
dc.creator.none.fl_str_mv Sánchez Díez, Eduardo
Vesga, Diana L.
Reyes Martín, Efraim
Uria Pujana, Uxue
Carrillo Fernández, María Luisa
Vicario Hernando, José Luis
author Sánchez Díez, Eduardo
author_facet Sánchez Díez, Eduardo
Vesga, Diana L.
Reyes Martín, Efraim
Uria Pujana, Uxue
Carrillo Fernández, María Luisa
Vicario Hernando, José Luis
author_role author
author2 Vesga, Diana L.
Reyes Martín, Efraim
Uria Pujana, Uxue
Carrillo Fernández, María Luisa
Vicario Hernando, José Luis
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv asymetric-synthesis
alpha,beta-unsaturated aldehydes
formylcyclopropane 1,1 diesters
chiral pyrrolizines
aldol reactions
3+2 annulation
silyl ethers
derivatives
cycloaddition
construction
topic asymetric-synthesis
alpha,beta-unsaturated aldehydes
formylcyclopropane 1,1 diesters
chiral pyrrolizines
aldol reactions
3+2 annulation
silyl ethers
derivatives
cycloaddition
construction
description An easy and straightforward procedure has been developed for the synthesis of highly enantioenriched pyrrolo-[1,2-a]quinolines through a one-pot process that comprises a domino cyclopropane ring opening/aza-Michael/aldol reaction followed by acid-promoted lactamization. The key feature of the synthetic approach relies on the ability of conveniently functionalized cyclopropaneacetaldehydes to undergo organocatalytic activation by a chiral secondary amine that enables the catalytic generation of a donor acceptor cyclopropane. This intermediate has the potential to undergo a ring opening that generates an electrophilic alpha,beta-unsaturated iminium ion that subsequently reacts through the already mentioned domino sequence and in which stereochemical information is very efficiently transferred from the amine catalyst to the final products. Moreover, one of the alkoxycarbonyl moieties can be easily removed by standard hydrolysis/decarboxylation, providing access to the target adducts as single stereoisomers.
publishDate 2016
dc.date.none.fl_str_mv 2016
2018
2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/25991
url http://hdl.handle.net/10810/25991
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MINECO/FEDER-CTQ2014-52107-P/
https://pubs.acs.org/doi/10.1021/acs.orglett.6b00173
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
Atribución-NoComercial-SinDerivadas 3.0 España
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/3.0/es/
Atribución-NoComercial-SinDerivadas 3.0 España
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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