Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates

Detalhes bibliográficos
Autor(a) principal: Soto, Martín
Data de Publicação: 2018
Outros Autores: Soengas, Raquel G., Silva, Artur M.S., Gotor-Fernández, Vicente, Rodríguez-Solla, Humberto
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/37531
Resumo: A general and highly selective method for the synthesis of carbohydrate-derived (Z)-vinyl halides and silanes is described. This reaction takes place through a β-elimination process of sugar-derived α-halomethylcarbinol acetates promoted by samarium diiodide. Starting materials have been easily prepared in two steps consisting in an initial addition of halomethyllithium compounds to the corresponding galactose-derived aldehyde, followed by acetylation. A mechanism that explains both the formation of (Z)-vinyl derivatives and its selectivity is proposed. Finally, the synthetic usefulness of these compounds has been applied in cross-coupling reactions with ethynyl benzene towards the formation of selected enyne derivatives.
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spelling Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetatesCarbohydratesEliminationSamariumSilanesSonogashira reactionStereoselectivityVinyl halidesA general and highly selective method for the synthesis of carbohydrate-derived (Z)-vinyl halides and silanes is described. This reaction takes place through a β-elimination process of sugar-derived α-halomethylcarbinol acetates promoted by samarium diiodide. Starting materials have been easily prepared in two steps consisting in an initial addition of halomethyllithium compounds to the corresponding galactose-derived aldehyde, followed by acetylation. A mechanism that explains both the formation of (Z)-vinyl derivatives and its selectivity is proposed. Finally, the synthetic usefulness of these compounds has been applied in cross-coupling reactions with ethynyl benzene towards the formation of selected enyne derivatives.Elsevier2023-05-05T10:33:33Z2018-09-20T00:00:00Z2018-09-20info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/37531eng0040-402010.1016/j.tet.2018.05.002Soto, MartínSoengas, Raquel G.Silva, Artur M.S.Gotor-Fernández, VicenteRodríguez-Solla, Humbertoinfo: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:RCAAP2024-02-22T12:12:35Zoai:ria.ua.pt:10773/37531Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:08:09.248124Repositório 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 Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
title Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
spellingShingle Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
Soto, Martín
Carbohydrates
Elimination
Samarium
Silanes
Sonogashira reaction
Stereoselectivity
Vinyl halides
title_short Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
title_full Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
title_fullStr Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
title_full_unstemmed Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
title_sort Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
author Soto, Martín
author_facet Soto, Martín
Soengas, Raquel G.
Silva, Artur M.S.
Gotor-Fernández, Vicente
Rodríguez-Solla, Humberto
author_role author
author2 Soengas, Raquel G.
Silva, Artur M.S.
Gotor-Fernández, Vicente
Rodríguez-Solla, Humberto
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Soto, Martín
Soengas, Raquel G.
Silva, Artur M.S.
Gotor-Fernández, Vicente
Rodríguez-Solla, Humberto
dc.subject.por.fl_str_mv Carbohydrates
Elimination
Samarium
Silanes
Sonogashira reaction
Stereoselectivity
Vinyl halides
topic Carbohydrates
Elimination
Samarium
Silanes
Sonogashira reaction
Stereoselectivity
Vinyl halides
description A general and highly selective method for the synthesis of carbohydrate-derived (Z)-vinyl halides and silanes is described. This reaction takes place through a β-elimination process of sugar-derived α-halomethylcarbinol acetates promoted by samarium diiodide. Starting materials have been easily prepared in two steps consisting in an initial addition of halomethyllithium compounds to the corresponding galactose-derived aldehyde, followed by acetylation. A mechanism that explains both the formation of (Z)-vinyl derivatives and its selectivity is proposed. Finally, the synthetic usefulness of these compounds has been applied in cross-coupling reactions with ethynyl benzene towards the formation of selected enyne derivatives.
publishDate 2018
dc.date.none.fl_str_mv 2018-09-20T00:00:00Z
2018-09-20
2023-05-05T10:33:33Z
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/10773/37531
url http://hdl.handle.net/10773/37531
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0040-4020
10.1016/j.tet.2018.05.002
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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