Regioselectivity in the Lithiation ofO-(4-Methoxyphenyl)-N,N-diethylthiocarbamate: Relative Directed Metalation Abilities of Methoxy and N,N-diethylthiocarbamate Functionalities

Directed ortho metalation is a useful approach to the regioselective synthesis of polysubstituted aromatics.1 The regioselectivity of the metalation can depend, in some instances, on the relative positions and directing abilities of two or more functional groups, and studies to establish the relative directing abilities of ortho metalation groups have been reported.1 The O-aryl carbamates are particularly powerful ortho-metalation directors and have been employed effectively in the construction of a variety of polysubstituted aromatic compounds.1,2