| 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 |
| Autores |
Boyd, Derek R. , Sharma, Narain D. , MOREJÓN LLAMAS, NOEMÍ, O'Dowd, Colin R. , Allen, Christopher C. R. |
| Publicación externa |
Si |
| Medio |
ORGANIC & BIOMOLECULAR CHEMISTRY |
| 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. |
| Miembros de la Universidad Loyola |
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