title: Chemoenzymatic synthesis of the trans-dihydrodiol isomers of monosubstituted benzenes via anti-benzene dioxides.
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.
authors.affiliation: School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast BT9 5AG, UK.
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: Nuria M
authors.initials: NM
authors.lastname: Llamas
authors.forename: Colin R
authors.initials: CR
authors.lastname: O'Dowd
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001555:Benzene Derivatives; D009281:Naphthalenes; C507866:trans-1,2-dihydro-1,2-naphthalenediol