| Title |
Chemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers |
| Authors |
Boyd, Derek R. , Sharma, Narain D. , MOREJÓN LLAMAS, NOEMÍ, Coen, Gerard P. , McGeehin, Peter K. M. , Allen, Christopher C. R. |
| External publication |
Si |
| Means |
ORGANIC & BIOMOLECULAR CHEMISTRY |
| Scope |
Article |
| Nature |
Científica |
| JCR Quartile |
1 |
| SJR Quartile |
1 |
| JCR Impact |
3.167 |
| SJR Impact |
1.88 |
| Publication date |
01/01/2007 |
| ISI |
000243746100019 |
| DOI |
10.1039/b616100f |
| Abstract |
Enantiopure trans-dihydrodiols have been obtained by a chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites, obtained by dioxygenase-catalysed arene cis-dihydroxylation at the 2,3-bond of monosubstituted benzene substrates. This generally applicable, seven-step synthetic route to trans-dihydrodiols involves a regioselective hydrogenation and a Mitsunobu inversion of configuration at C-2, followed by benzylic bromination and dehydrobromination steps. The method has also been extended to the synthesis of both enantiomers of the trans-dihydrodiol derivatives of toluene, through substitution of a vinyl bromine atom of the corresponding trans-dihydrodiol enantiomers derived from bromobenzene. Through incorporation of hydrogenolysis and diMTPA ester diastereoisomer resolution steps into the synthetic route, both trans-dihydrodiol enantiomers of monohalobenzenes were obtained from the cis-dihydrodiols of 4-haloiodobenzenes. |
| Universidad Loyola members |
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