A study of substrate specificity of toluene dioxygenase in processing aromatic compounds containing benzylic and/or remote chiral centers

A series of substituted arenes containing remote chiral centers were screen ed as substrates for toluene dioxygenase (TDO). The absolute stereochemistr y of the new metabolites was determined by chemical and spectroscopic corre lation with synthetic standards. There was no evidence for kinetic resoluti on; enantiomers were indiscriminately processed by the enzyme to diastereom eric pairs, which were separable upon derivatization. Some of these new met abolites are useful as synthons for morphine synthesis. Full experimental d etails are reported for those new compounds stable to isolation and for der ivatives of those that are unstable.