Lithiated <i>N</i>‐pivaloyl‐tetrahydroisoquinoline—a Supernuclephile

The high nucleophilicity of the lithium derivative of (1), X = COtBu, permits alkylation at C-1 using primary alkyl chlorides, secondary alkyl iodides or easily deprotonated ketones. The pivaloyl group in the product (2) can be reductively removed. 1,1-Disubstituted tetra-hydroisoquinolines such as (3) can be obtained in this way.