Controlling the regioselectivity of lithiation using kinetic isotope effects: Deuterium as a protecting group for carbon

Article abstract of DOI:10.1016/S0040-4039(98)01930-3

By substituting deuterium for hydrogen at positions of high kinetic acidity in amides and carbamates, the usual regiochemical course of their reactions with alkyllithiums (ortholithiation vs. lateral lithiation vs. nucleophilic addition) can be altered or overturned by the kinetic isotope effect. The deuterium substituent functions in these reactions as a protecting group for carbon.