A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
| Autor: | Costa, Jeronimo S., Freire, Bruno S., Moura, André L. S., Pereira, Vera L. Patrocinio |
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| Jazyk: | angličtina |
| Rok vydání: | 2006 |
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| Zdroj: | Journal of the Brazilian Chemical Society v.17 n.7 2006 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ Journal of the Brazilian Chemical Society, Volume: 17, Issue: 7, Pages: 1229-1232, Published: DEC 2006 |
| Popis: | The reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b,c were transformed via Nef reaction into (R)-carvone ketone derivatives 9,10 and nitroadducts 2b,d led to (R)-carvone alkylated derivatives 11,12, via a denitration reaction. A reatividade e diastereosseletividade da adição conjugada de íons nitronatos representativos à (R)-carvona foi estudada. Os adutos de Michael 2a-e foram obtidos em bom rendimento e boa 3,2-cis-3,5-trans-seletividade. Os nitroadutos 2b e 2c foram transformados via uma reação de Nef nos ceto-derivados 9 e 10 ao passo que uma reação de desnitração transformou 2b e 2d nos derivados alquilados da carvona 11 e 12. |
| Databáze: | OpenAIRE |
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