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...
| Authors: | ; ; ; ; ; ; |
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| Format: | Article |
| Status: | Accepted version |
| Publication date: | 2014 |
| Country: | España |
| Institution: | Universidad de Barcelona |
| Repository: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/169228 |
| Online Access: | https://hdl.handle.net/2445/169228 |
| Access Level: | Open access |
| Keyword: | Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| _version_ | 1878742027222384640 |
|---|---|
| author | Fàbregas, Mireia |
| 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 |
| author_browse | Font Bardia, Ma. Mercedes Fàbregas, Mireia Gómez Palomino, Alejandro Pellicena Zanón, Miquel Reina, D.F. Romea, Pedro Urpí Tubella, Fèlix |
| 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 |
| collection | Dipòsit Digital de la UB |
| 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. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | ES_eefb845645bd7efd4e4e7ce53c9f36db |
| institution | Universidad de Barcelona |
| instname_str | Universidad de Barcelona |
| network_acronym_str | ES |
| network_name_str | España |
| oai_identifier_str | oai:diposit.ub.edu:2445/169228 |
| publishDate | 2014 |
| publishDateSort | 2014 |
| publisher | American Chemical Society |
| publisherStr | American Chemical Society |
| reponame_str | Dipòsit Digital de la UB |
| spelling | Substrate-controlled Michael additions of chiral ketones to enones Fàbregas, Mireia Gómez Palomino, Alejandro Pellicena Zanón, Miquel Reina, D.F. Romea, Pedro Urpí Tubella, Fèlix Font Bardia, Ma. Mercedes Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones 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. American Chemical Society https://hdl.handle.net/2445/169228 |
| spellingShingle | Substrate-controlled Michael additions of chiral ketones to enones Fàbregas, Mireia Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| status_str | acceptedVersion |
| title | 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_short | Substrate-controlled Michael additions of chiral ketones to enones |
| title_sort | Substrate-controlled Michael additions of chiral ketones to enones |
| topic | Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| topic_facet | Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| url | https://hdl.handle.net/2445/169228 |