Publicação
Synthesis of carbohydrate-derived (Z)-vinyl halides and silanes: samarium-promoted stereoselective 1,2-elimination on sugar-derived α-halomethylcarbinol acetates
| 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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| Autores principais: | Soto, Martín |
| Outros Autores: | Soengas, Raquel G.; Silva, Artur M.S.; Gotor-Fernández, Vicente; Rodríguez-Solla, Humberto |
| Assunto: | Carbohydrates Elimination Samarium Silanes Sonogashira reaction Stereoselectivity Vinyl halides |
| Ano: | 2018 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade de Aveiro |
| Idioma: | inglês |
| Origem: | RIA - Repositório Institucional da Universidade de Aveiro |
| 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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