| Título | syn-Benzene dioxides: chemoenzymatic synthesis from 2,3-cis-dihydrodiol derivatives of monosubstituted benzenes and their application in the synthesis of regioisomeric 1,2-and 3,4-cis-dihydrodiols and 1,4-dioxocins |
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| Autores | Boyd, Derek R. , Sharma, Narain D. , MOREJÓN LLAMAS, NOEMÍ, O'Dowd, Colin R. , Allen, Christopher C. R. |
| Publicación externa | Si |
| Medio | Org. Biomol. Chem. |
| Alcance | Article |
| Naturaleza | Científica |
| Cuartil JCR | 1 |
| Cuartil SJR | 1 |
| Impacto JCR | 3.167 |
| Impacto SJR | 1.88 |
| Fecha de publicacion | 01/01/2007 |
| ISI | 000247768900024 |
| DOI | 10.1039/b704584k |
| Abstract | cis-2,3-Dihydrodiol metabolites of monosubstituted halobenzenes and toluene have been used as synthetic precursors of the corresponding 3,4-cis-dihydrodiols. Enantiopure syn-benzene dioxide intermediates were reduced to the 3,4-cis-dihydrodiols and thermally racemised via the corresponding 1,4-dioxocins. The syn-benzene dioxide-1,4-dioxocin valence tautomeric equilibrium ratio was found to be dependent on the substituent position. The methodology has also been applied to the synthesis of both enantiomers of the 1,2-(ipso)- and 3,4-cis-dihydrodiols of toluene. This chemoenzymatic approach thus makes available, for the first time, all three possible cis-dihydrodiol regioisomers of a monosubstituted benzene. |
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