First direct C-2-Lithiation of 4-DMAP. Convenient access to reactive functional derivatives and ligands.

The first direct alpha-lithiation of 4-DMAP has been performed via reaction with the BuLi-Me(2)N(CH(2))(2)OLi (BuLi-LiDMAE) reagent. This new methodology avoids the use of a activation-lithiation-regeneration sequence or halogen-metal exchange classically employed. New useful DMAP-containing synthons and polyheterocycles have been efficiently prepared.