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Synthesis 1991; 1991(12): 1221-1227
DOI: 10.1055/s-1991-28423
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Remote Controlled Nucleophilicity, 21: Lithiated Cα-Substituted 4-Methylpyridines

Ernst Anders* , Andreas Opitz, Walter Bauer
  • *Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestraße 42, D-8520 Erlangen, Germany
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Publication Date:
29 April 2002 (online)

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

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