Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement

Bibliographic Details
Main Author: Lopes, Susana M. M.
Publication Date: 2009
Other Authors: Santos, Bruna S., Palacios, Francisco, Melo, Teresa M. V. D. Pinho e
Format: Article
Language: eng
Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Download full: https://hdl.handle.net/10316/110169
https://doi.org/10.3998/ark.5550190.0011.508
Summary: The reactivity of allenic esters towards an activated N-sulfonylimine and electron-deficient alkenes with a phosphine under microwave irradiation is explored. The methodology is shown to be efficient for the one-step synthesis of 3-pyrrolines and cyclopentenes in a regio- and diastereoselective manner. This formal [3+2] cycloaddition is complete within five minutes. It was also demonstrated that microwave irradiation is the best energy source to carry out the Lewis acid catalyzed allenoate-Claisen rearrangement leading to 3-(pyrrolidin-1-yl)hepta-2,6-dienoates.
id RCAP_6f6a61f37473ac4549b5876dd292d526
oai_identifier_str oai:estudogeral.uc.pt:10316/110169
network_acronym_str RCAP
network_name_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository_id_str https://opendoar.ac.uk/repository/7160
spelling Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangementMicrowave-assisted reactions, [3+2] anellationallenoate-Claisen rearrangement3-pyrrolinescyclopenteneshepta-2,6-dienoatesThe reactivity of allenic esters towards an activated N-sulfonylimine and electron-deficient alkenes with a phosphine under microwave irradiation is explored. The methodology is shown to be efficient for the one-step synthesis of 3-pyrrolines and cyclopentenes in a regio- and diastereoselective manner. This formal [3+2] cycloaddition is complete within five minutes. It was also demonstrated that microwave irradiation is the best energy source to carry out the Lewis acid catalyzed allenoate-Claisen rearrangement leading to 3-(pyrrolidin-1-yl)hepta-2,6-dienoates.Arkat USA2009info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://hdl.handle.net/10316/110169https://hdl.handle.net/10316/110169https://doi.org/10.3998/ark.5550190.0011.508eng1551-7012Lopes, Susana M. M.Santos, Bruna S.Palacios, FranciscoMelo, Teresa M. V. D. Pinho einfo:eu-repo/semantics/openAccessreponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2023-11-16T09:31:25Zoai:estudogeral.uc.pt:10316/110169Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-29T06:01:50.185185Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
dc.title.none.fl_str_mv Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
title Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
spellingShingle Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
Lopes, Susana M. M.
Microwave-assisted reactions, [3+2] anellation
allenoate-Claisen rearrangement
3-pyrrolines
cyclopentenes
hepta-2,6-dienoates
title_short Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
title_full Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
title_fullStr Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
title_full_unstemmed Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
title_sort Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement
author Lopes, Susana M. M.
author_facet Lopes, Susana M. M.
Santos, Bruna S.
Palacios, Francisco
Melo, Teresa M. V. D. Pinho e
author_role author
author2 Santos, Bruna S.
Palacios, Francisco
Melo, Teresa M. V. D. Pinho e
author2_role author
author
author
dc.contributor.author.fl_str_mv Lopes, Susana M. M.
Santos, Bruna S.
Palacios, Francisco
Melo, Teresa M. V. D. Pinho e
dc.subject.por.fl_str_mv Microwave-assisted reactions, [3+2] anellation
allenoate-Claisen rearrangement
3-pyrrolines
cyclopentenes
hepta-2,6-dienoates
topic Microwave-assisted reactions, [3+2] anellation
allenoate-Claisen rearrangement
3-pyrrolines
cyclopentenes
hepta-2,6-dienoates
description The reactivity of allenic esters towards an activated N-sulfonylimine and electron-deficient alkenes with a phosphine under microwave irradiation is explored. The methodology is shown to be efficient for the one-step synthesis of 3-pyrrolines and cyclopentenes in a regio- and diastereoselective manner. This formal [3+2] cycloaddition is complete within five minutes. It was also demonstrated that microwave irradiation is the best energy source to carry out the Lewis acid catalyzed allenoate-Claisen rearrangement leading to 3-(pyrrolidin-1-yl)hepta-2,6-dienoates.
publishDate 2009
dc.date.none.fl_str_mv 2009
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://hdl.handle.net/10316/110169
https://hdl.handle.net/10316/110169
https://doi.org/10.3998/ark.5550190.0011.508
url https://hdl.handle.net/10316/110169
https://doi.org/10.3998/ark.5550190.0011.508
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1551-7012
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Arkat USA
publisher.none.fl_str_mv Arkat USA
dc.source.none.fl_str_mv reponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
_version_ 1833602554133479424

Similar Items