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Synlett 1994; 1994(8): 609-610
DOI: 10.1055/s-1994-22944
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Directing Effect of 1,3-Dimethylimidazolidine in Ortho Lithiation Changes with Its Vicinal Group

Eiko Tamura* , Ken-ichi Kawasaki, Daisuke Mikame, Tsutomu Katsuki
  • *Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812, Japan
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Publication Date:
18 September 2002 (online)

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Directing effect of 1,3-dimethylimidazolidine in ortho lithiation is changed by the presence of vicinal phenolic hydroxy group probably due to the chelate formation. Lithiation of 1,3-dimethylimidazolidine derivative of salicylaldehyde occurs not ortho to 1,3-dimethylimidazolidine but ortho to hydroxy group, though 1,3-dimethylimidazolidine is a stronger directing group than hydroxy group.