title: Palladium-catalyzed carbonylation of halo arene-cis-dihydrodiols to the corresponding carboxylates. Access to compounds unavailable by toluene dioxygenase-mediated dihydroxylation of the corresponding benzoate esters.
abstract: A series of arene-cis-dihydrodiol carboxylates was prepared by palladium-catalyzed carbonylation of (1S, 2S-cis)-3-iodo-3,5-cyclohexadiene-1,2-diol, which is obtained in high titers by enzymatic dihydroxylation of iodobenzene. Both the free diol and the corresponding acetonide were subjected to this protocol to produce various arene-cis-dihydrodiol carboxylates that are unavailable by fermentation of the corresponding benzoates or are produced in low yields. The comparison of yields obtained from fermentation versus carbonylation was made for all compounds investigated. Experimental and spectral data are provided for all new compounds.
authors.affiliation: Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada. thudlicky@brocku.ca.
authors.forename: Jordan
authors.initials: J
authors.lastname: Froese
authors.forename: Jason Reed
authors.initials: JR
authors.lastname: Hudlicky
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D004952:Esters; D006018:Glycols / Q000737:chemistry*; D006900:Hydroxylation; D010105:Oxygenases / Q000378:metabolism*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001565:Benzoates; D002264:Carboxylic Acids; D004952:Esters; D006018:Glycols; D010165:Palladium; D010105:Oxygenases; C023172:toluene dioxygenase