Enzymatic oxidation of para-substituted arenes: Access to new non-racemic chiral metabolites for synthesis

John F. Trant, Brock University
Jordan Froese, Brock University
Tomas Hudlicky, Brock University

Abstract

A series of para-substituted benzene derivatives were subjected to whole-cell fermentation with Escherichia coli JM109 (pDTG601), an organism expressing toluene dioxygenase (TDO). Several compounds proved to be excellent substrates for TDO, including 4-bromo-phenylacetylene, 4-bromobenzaldehyde, 4-bromobenzyl alcohol and 4-bromo-allylbenzene. Some of the first para-functionalized diene diols produced using TDO, are useful substrates for further synthetic manipulations, including their use in the potential synthesis of complex natural products. © 2013 Elsevier Ltd. All rights reserved.