Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Chiral Host. Attempted Synthesis Using McMurry Reaction as a Final Ring Closure Method

  • Kyung-Soo Paek (Department of Chemistry, Korea Institute of Science and Technology) ;
  • Donald J. Cram (Department of Chemistry and Biochemistry, University of Californis)
  • Published : 1989.12.20
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Abstract

Using the low valent titanium induced carbonyl-carbonyl coupling reaction, it was attempted to synthesize sterically hindered 17-membered cyclic chiral host 2. The semifinal dialdehyde 12 was obtained through 11 step reactions beginning from p-tert-butylphenol and dibenzofuran. When dialdehyde 12 was treated with $TiCl_3-Zn/Cu,$ only intermolecularly coupled dimer 14 was obtained instead of intramolecularly coupled cyclic alkene 2. The mechanistic consideration leading to 14 was discussed and the cation binding properties of dimer 14 and dicarboxylic intermediate 13 was reported, which implies the significance of the principle of preorganization of host's binding sites prior to complexation.

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References

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  1. ChemInform Abstract: Chiral Host. Attempted Synthesis Using McMurry Reaction as a Final Ring‐Closure Method. vol.21, pp.22, 1990, https://doi.org/10.1002/chin.199022115