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 documento: | Artigo |
| Estado: | Accepted version |
| Data de publicação: | 2014 |
| País: | España |
| Recursos: | Universidad de Barcelona |
| Repositório: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/169228 |
| Acesso em linha: | https://hdl.handle.net/2445/169228 |
| Nível de acesso: | Acesso aberto |
| Palavra-chave: | Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
| Resumo: | 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. |
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