One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment

Detalhes bibliográficos
Autor(a) principal: Soares, Maria I. L.
Data de Publicação: 2019
Outros Autores: Lopes, Susana M. M., Murtinho, Dina, Pinho e Melo, Teresa M. V. D.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/90774
https://doi.org/10.21577/0100-4042.20170448
Resumo: A one-pot diastereoselective synthesis of thiazolidine-ring fused systems derived from enantiomerically pure amino acids, L-cysteine or D-penicillamine, and achiral succindialdehyde is described as an experiment to be carried out by upper-division undergraduate students in a laboratory classroom. Reactions were performed under mild conditions, the products were isolated through simple experimental procedures and fully characterized. This study combines organic synthesis, determination of the purity of compounds (TLC analysis and melting point measurements), optical activity measurements as well as structural analysis (interpretation of 1D NMR and 2D NMR spectra). It offers a platform for the discussion of important organic chemistry concepts such as diastereoselectivity, kinetic control vs thermodynamic control and cyclization reactions via nucleophilic addition to imines/iminium cations.
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spelling One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experimentOrganic chemistryHeterocyclesThiazolidineDiastereoselective synthesisChiral poolNMR spectroscopyA one-pot diastereoselective synthesis of thiazolidine-ring fused systems derived from enantiomerically pure amino acids, L-cysteine or D-penicillamine, and achiral succindialdehyde is described as an experiment to be carried out by upper-division undergraduate students in a laboratory classroom. Reactions were performed under mild conditions, the products were isolated through simple experimental procedures and fully characterized. This study combines organic synthesis, determination of the purity of compounds (TLC analysis and melting point measurements), optical activity measurements as well as structural analysis (interpretation of 1D NMR and 2D NMR spectra). It offers a platform for the discussion of important organic chemistry concepts such as diastereoselectivity, kinetic control vs thermodynamic control and cyclization reactions via nucleophilic addition to imines/iminium cations.Sociedade Brasileira de Química2019-11-21info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/90774http://hdl.handle.net/10316/90774https://doi.org/10.21577/0100-4042.20170448eng0100-40421678-7064 (online)http://quimicanova.sbq.org.br/detalhe_artigo.asp?id=7004Soares, Maria I. L.Lopes, Susana M. M.Murtinho, DinaPinho e Melo, Teresa M. V. D.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-05-25T05:37:17Zoai:estudogeral.uc.pt:10316/90774Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:10:48.618550Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
title One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
spellingShingle One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
Soares, Maria I. L.
Organic chemistry
Heterocycles
Thiazolidine
Diastereoselective synthesis
Chiral pool
NMR spectroscopy
title_short One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
title_full One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
title_fullStr One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
title_full_unstemmed One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
title_sort One-pot diastereoselective synthesis of chiral tricyclic L-cysteine and D-penicillamine derivatives: a laboratory experiment
author Soares, Maria I. L.
author_facet Soares, Maria I. L.
Lopes, Susana M. M.
Murtinho, Dina
Pinho e Melo, Teresa M. V. D.
author_role author
author2 Lopes, Susana M. M.
Murtinho, Dina
Pinho e Melo, Teresa M. V. D.
author2_role author
author
author
dc.contributor.author.fl_str_mv Soares, Maria I. L.
Lopes, Susana M. M.
Murtinho, Dina
Pinho e Melo, Teresa M. V. D.
dc.subject.por.fl_str_mv Organic chemistry
Heterocycles
Thiazolidine
Diastereoselective synthesis
Chiral pool
NMR spectroscopy
topic Organic chemistry
Heterocycles
Thiazolidine
Diastereoselective synthesis
Chiral pool
NMR spectroscopy
description A one-pot diastereoselective synthesis of thiazolidine-ring fused systems derived from enantiomerically pure amino acids, L-cysteine or D-penicillamine, and achiral succindialdehyde is described as an experiment to be carried out by upper-division undergraduate students in a laboratory classroom. Reactions were performed under mild conditions, the products were isolated through simple experimental procedures and fully characterized. This study combines organic synthesis, determination of the purity of compounds (TLC analysis and melting point measurements), optical activity measurements as well as structural analysis (interpretation of 1D NMR and 2D NMR spectra). It offers a platform for the discussion of important organic chemistry concepts such as diastereoselectivity, kinetic control vs thermodynamic control and cyclization reactions via nucleophilic addition to imines/iminium cations.
publishDate 2019
dc.date.none.fl_str_mv 2019-11-21
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 http://hdl.handle.net/10316/90774
http://hdl.handle.net/10316/90774
https://doi.org/10.21577/0100-4042.20170448
url http://hdl.handle.net/10316/90774
https://doi.org/10.21577/0100-4042.20170448
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0100-4042
1678-7064 (online)
http://quimicanova.sbq.org.br/detalhe_artigo.asp?id=7004
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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