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Synthesis 1996; 1996(6): 702-706
DOI: 10.1055/s-1996-4280
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Synthesis of Chiral Thienylpyridines from Naturally Occurring Monoterpenes: Useful Ligands for Cyclometallated Complexes

Michel Gianini, Alex von Zelewsky*
  • *Institute of Inorganic Chemistry, University of Fribourg, Pérolles, CH-1700 Fribourg, Switzerland, Fax +41(37)299738
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Publication Date:
31 December 2000 (online)

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On treatment with ammonium acetate, α,β-unsaturated ketones or aldehydes can easily undergo condensation with acetylpyridinium salts (Kröhnke reaction). Four ”thienylpyridine” ligands, derived from (-)-β-pinene, (+)-camphor, (+)-3-carene and (+)-2-carene, were prepared according to this method. The multistep syntheses to get (1R,5R)-3-methyleneopinone (5), (+)-3-methylenecamphor (10), (-)-3-caren-10-al (15) and (1S,6R)-7,7-dimethyl-3-methylenebicyclo[4.1.0]heptan-2-one (18) are also described.

A,B-unsaturated ketones and aldehydes - Kröhnke reaction - chiral ligands