Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: Synthesis of benzo[b]thiophene 2,3-oxide
Enzymatic cis-dihydroxylation of benzo[b]thiophene, benzo[b]furan and several methyl substituted derivatives was found to occur in both the carbocyclic and heterocyclic rings. Relative and absolute configurations and enantiopurities of the resulting dihydrodiols were determined. Hydrogenation of the alkene bond in carbocyclic cis-dihydrodiols and ring-opening epimerization/reduction reactions of heterocyclic cis/trans-dihydrodiols were also studied. The relatively stable heterocyclic dihydrodiols of benzo[b]thiophene and benzo[b]furan showed a strong preference for the trans configuration in aqueous solutions. The 2,3-dihydrodiol metabolite of benzo[b]thiophene was utilized as a precursor in the chemoenzymatic synthesis of the unstable arene oxide, benzo[b]thiophene 2,3-oxide.
Boyd, Derek R.,Sharma, Narain D.,Brannigan, Ian N.,Evans, Timothy A.,Haughey, Simon A.,McMurray, Brian T.,Malone, John F.,McIntyre, Peter B. A.,Stevenson, Paul J.,Allen, Christopher C. R.
scheme or table
p. 7292 - 7304
(2012/10/07)
Stereoselective Synthesis of Optically Active 2-Hydroxymandelic Acids and Esters via Friedel-Crafts Coordinated Reaction: Crystal Structure of Chiral Dichloro[2-(1-oxido-1-menthoxycarbonylmethyl)-4-methoxyphenoxido-O,O,O] titanium?
Highly diastereoselective hydroxyalkylation of phenols with chiral glyoxylates was performed. Hydrolysis or reduction of the esters 3 afforded 2-hydroxymandelic acids 6 and diols 5 in high yields and enantiomeric pure form. Mechanistic evidence of chelati
Bigi, Franca,Bocelli, Gabriele,Maggi, Raimondo,Sartori, Giovanni
p. 5004 - 5009
(2007/10/03)
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