Título Chemoenzymatic synthesis of the trans-dihydrodiol isomers of monosubstituted benzenes via anti-benzene dioxides
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 2
Cuartil SJR 1
Impacto JCR 2.87400
Impacto SJR 1.59400
Fecha de publicacion 01/01/2006
ISI 237907500014
DOI 10.1039/b603928f
Abstract Enantiopure cis-2,3-dihydrodiols, available from dioxygenase-catalysed cis-dihydroxylation of monosubstituted benzene substrates, have been used as synthetic precursors of the corresponding trans-3,4-dihydrodiols. The six-step chemoenzymatic route from cis-dihydrodiol precursors, involving acetonide, tetraol, dibromodiacetate and diepoxide intermediates, and substitution of vinyl bromide and iodide atoms, has been used in the synthesis of ten trans-dihydrododiol derivatives of substituted benzenes. The general applicability of the method has been demonstrated by its use in the synthesis of both enantiomers of the trans-1,2- and 3,4-dihydrodiol derivatives of toluene.
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