The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10−15 L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.

Cyclopropylbenzene was subjected to whole-cell fermentation with either Escherichia coli JM109 (pDTG601) or E. coli JM109 (pDTG602), expressing toluene dioxygenase and toluene dioxygenase – dihydrodiol dehydrogenase enzymes, respectively. The corresponding metabolites, 3-cyclopropylcyclohexa-3,5-diene-1,2-diol (3) and 3-cyclopropylbenzene-1,2-diol (5) have been isolated in yields of 2.5 and 1 g L–1, respectively. The absolute stereochemistry correlation for 3 is provided, along with a preliminary discussion of its potential in asymmetric synthesis. Possible mechanistic implications are indicated for the enzymatic oxygenation through the use of calculations. Experimental data are provided for all new compounds.Key words: cyclopropylbenzene, bio-oxidation, cis-diene diol, catechol, JM109 (pDTG601), JM109 (pDTG602), dioxygenase.