Contribution to the synthesis of chiral allenic esters
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2003 |
| Outros Autores: | , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| Texto Completo: | http://hdl.handle.net/10316/5157 https://doi.org/10.1016/S0040-4039(03)01585-5 |
Resumo: | A phosphorus ylide bearing a 10-phenylsulfonylisoborneol unit reacted with ketenes, generated in situ from acid chlorides and triethylamine, to give allenic compounds. The reaction with methylketene led to asymmetric induction with the selective synthesis of an allene with axial chirality corresponding to an S configuration. The structure of the chiral allene 10-phenylsulfonylisobornyl penta-2,3-dienoate was determined by X-ray crystallography. Chirooptical studies of the chiral allene derivatives were done. |
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Contribution to the synthesis of chiral allenic estersasymmetric Wittig reactionchiral alleneschiral phosphorus ylidesA phosphorus ylide bearing a 10-phenylsulfonylisoborneol unit reacted with ketenes, generated in situ from acid chlorides and triethylamine, to give allenic compounds. The reaction with methylketene led to asymmetric induction with the selective synthesis of an allene with axial chirality corresponding to an S configuration. The structure of the chiral allene 10-phenylsulfonylisobornyl penta-2,3-dienoate was determined by X-ray crystallography. Chirooptical studies of the chiral allene derivatives were done.http://www.sciencedirect.com/science/article/B6THS-495V85W-H/1/c946b9b7c8443e7586a0402c58d86df22003info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleaplication/PDFhttp://hdl.handle.net/10316/5157http://hdl.handle.net/10316/5157https://doi.org/10.1016/S0040-4039(03)01585-5engTetrahedron Letters. 44:34 (2003) 6409-6412Melo, Teresa M. V. D. Pinho eCardoso, Ana L.Gonsalves, António M. d'A. RochaStorr, Richard C.Pessoa, João CostaPaixão, José A.Beja, Ana M.Silva, Manuela Ramosinfo: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:RCAAP2021-09-02T11:10:16Zoai:estudogeral.uc.pt:10316/5157Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:40.865314Repositório 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 |
Contribution to the synthesis of chiral allenic esters |
| title |
Contribution to the synthesis of chiral allenic esters |
| spellingShingle |
Contribution to the synthesis of chiral allenic esters Melo, Teresa M. V. D. Pinho e asymmetric Wittig reaction chiral allenes chiral phosphorus ylides |
| title_short |
Contribution to the synthesis of chiral allenic esters |
| title_full |
Contribution to the synthesis of chiral allenic esters |
| title_fullStr |
Contribution to the synthesis of chiral allenic esters |
| title_full_unstemmed |
Contribution to the synthesis of chiral allenic esters |
| title_sort |
Contribution to the synthesis of chiral allenic esters |
| author |
Melo, Teresa M. V. D. Pinho e |
| author_facet |
Melo, Teresa M. V. D. Pinho e Cardoso, Ana L. Gonsalves, António M. d'A. Rocha Storr, Richard C. Pessoa, João Costa Paixão, José A. Beja, Ana M. Silva, Manuela Ramos |
| author_role |
author |
| author2 |
Cardoso, Ana L. Gonsalves, António M. d'A. Rocha Storr, Richard C. Pessoa, João Costa Paixão, José A. Beja, Ana M. Silva, Manuela Ramos |
| author2_role |
author author author author author author author |
| dc.contributor.author.fl_str_mv |
Melo, Teresa M. V. D. Pinho e Cardoso, Ana L. Gonsalves, António M. d'A. Rocha Storr, Richard C. Pessoa, João Costa Paixão, José A. Beja, Ana M. Silva, Manuela Ramos |
| dc.subject.por.fl_str_mv |
asymmetric Wittig reaction chiral allenes chiral phosphorus ylides |
| topic |
asymmetric Wittig reaction chiral allenes chiral phosphorus ylides |
| description |
A phosphorus ylide bearing a 10-phenylsulfonylisoborneol unit reacted with ketenes, generated in situ from acid chlorides and triethylamine, to give allenic compounds. The reaction with methylketene led to asymmetric induction with the selective synthesis of an allene with axial chirality corresponding to an S configuration. The structure of the chiral allene 10-phenylsulfonylisobornyl penta-2,3-dienoate was determined by X-ray crystallography. Chirooptical studies of the chiral allene derivatives were done. |
| publishDate |
2003 |
| dc.date.none.fl_str_mv |
2003 |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10316/5157 http://hdl.handle.net/10316/5157 https://doi.org/10.1016/S0040-4039(03)01585-5 |
| url |
http://hdl.handle.net/10316/5157 https://doi.org/10.1016/S0040-4039(03)01585-5 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
Tetrahedron Letters. 44:34 (2003) 6409-6412 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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aplication/PDF |
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