Substrate-controlled Michael additions of chiral ketones to enones
Substrate-controlled Michael additions of the titanium-(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. Lik...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2014 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/169228 |
| Acceso en línea: | https://hdl.handle.net/2445/169228 |
| Access Level: | acceso abierto |
| Palabra clave: | Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
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Substrate-controlled Michael additions of chiral ketones to enonesFàbregas, MireiaGómez Palomino, AlejandroPellicena Zanón, MiquelReina, D.F.Romea, PedroUrpí Tubella, FèlixFont Bardia, Ma. MercedesÀcids de LewisTitaniCetonesLewis acidsTitaniumKetonesSubstrate-controlled Michael additions of the titanium-(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. Likely, the nucleophilic species involved in such additions are bimetallic enolates that may add to enones through cyclic transition states. Finally, further studies indicate that a structurally related β-benzyloxy chiral ketone can also participate in such stereocontrolled conjugate additions.American Chemical Society2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/169228Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1021/ol503133jOrganic Letters, 2014, vol. 16, num. 23, p. 6220-6223https://doi.org/10.1021/ol503133j(c) American Chemical Society , 2014info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1692282026-05-27T06:46:51Z |
| dc.title.none.fl_str_mv |
Substrate-controlled Michael additions of chiral ketones to enones |
| title |
Substrate-controlled Michael additions of chiral ketones to enones |
| spellingShingle |
Substrate-controlled Michael additions of chiral ketones to enones Fàbregas, Mireia Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| title_short |
Substrate-controlled Michael additions of chiral ketones to enones |
| title_full |
Substrate-controlled Michael additions of chiral ketones to enones |
| title_fullStr |
Substrate-controlled Michael additions of chiral ketones to enones |
| title_full_unstemmed |
Substrate-controlled Michael additions of chiral ketones to enones |
| title_sort |
Substrate-controlled Michael additions of chiral ketones to enones |
| dc.creator.none.fl_str_mv |
Fàbregas, Mireia Gómez Palomino, Alejandro Pellicena Zanón, Miquel Reina, D.F. Romea, Pedro Urpí Tubella, Fèlix Font Bardia, Ma. Mercedes |
| author |
Fàbregas, Mireia |
| author_facet |
Fàbregas, Mireia Gómez Palomino, Alejandro Pellicena Zanón, Miquel Reina, D.F. Romea, Pedro Urpí Tubella, Fèlix Font Bardia, Ma. Mercedes |
| author_role |
author |
| author2 |
Gómez Palomino, Alejandro Pellicena Zanón, Miquel Reina, D.F. Romea, Pedro Urpí Tubella, Fèlix Font Bardia, Ma. Mercedes |
| author2_role |
author author author author author author |
| dc.subject.none.fl_str_mv |
Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| topic |
Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| description |
Substrate-controlled Michael additions of the titanium-(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. Likely, the nucleophilic species involved in such additions are bimetallic enolates that may add to enones through cyclic transition states. Finally, further studies indicate that a structurally related β-benzyloxy chiral ketone can also participate in such stereocontrolled conjugate additions. |
| publishDate |
2014 |
| dc.date.none.fl_str_mv |
2014 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion |
| format |
article |
| status_str |
acceptedVersion |
| dc.identifier.none.fl_str_mv |
https://hdl.handle.net/2445/169228 |
| url |
https://hdl.handle.net/2445/169228 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
Versió postprint del document publicat a: https://doi.org/10.1021/ol503133j Organic Letters, 2014, vol. 16, num. 23, p. 6220-6223 https://doi.org/10.1021/ol503133j |
| dc.rights.none.fl_str_mv |
(c) American Chemical Society , 2014 info:eu-repo/semantics/openAccess |
| rights_invalid_str_mv |
(c) American Chemical Society , 2014 |
| eu_rights_str_mv |
openAccess |
| 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 |
Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) reponame:Dipòsit Digital de la UB instname:Universidad de Barcelona |
| instname_str |
Universidad de Barcelona |
| reponame_str |
Dipòsit Digital de la UB |
| collection |
Dipòsit Digital de la UB |
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|
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|
| _version_ |
1869423796197261312 |
| score |
15,300724 |