Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

…, V Ljubez, PKM McGeehin, PJ Stevenson…

Index: Boyd, Derek R.; Sharma, Narain D.; Ljubez, Vera; McGeehin, Peter K. M.; Stevenson, Paul J.; Blain, Marine; Allen, Christopher C. R. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 18 p. 3020 - 3029

Full Text: HTML

Citation Number: 2

Abstract

Enantiopure cis-dihydrodiol bacterial metabolites of substituted benzene substrates were used as precursors, in a chemoenzymatic synthesis of the corresponding benzene oxides and of a substituted oxepine, via dihydrobenzene oxide intermediates. A rapid total racemization of the substituted benzene 2, 3-oxides was found to have occurred, via their oxepine valence tautomers, in accord with predictions and theoretical calculations. ...