Remote controlled nucleophilicity, 2: Lithiated C(α)-substituted 4-methylpyridines

Article abstract of DOI:10.1055/s-1991-28423

C(α)-substituted 4-methylpyridines have been N-lithiated and reacted with chlorotrimethylsilane and other electrophiles. The lithiated C(α)-NMe₂ substituted intermediate shows an interesting dichotomy of behavior towards electrophiles: It represents the borderline between compounds for which an extreme N or C(α) regionucleophilicity is observed.