Titanium Alkoxide-Based Method for Stereoselective Synthesis of Functionalized Conjugated Dienes

@article{Hamada1999TitaniumAM,
  title={Titanium Alkoxide-Based Method for Stereoselective Synthesis of Functionalized Conjugated Dienes},
  author={T. Hamada and D. Suzuki and H. Urabe and F. Sato},
  journal={Journal of the American Chemical Society},
  year={1999},
  volume={121},
  pages={7342-7344}
}
Treatment of an internal acetylene such as 1-silyl-1-octyne (3) with a low-valent titanium reagent, (η2-propene)Ti(O-i-Pr)2 (1) readily prepared from Ti(O-i-Pr)4 and i-PrMgCl in situ, generates an acetylene−titanium complex. This complex was allowed to react with a terminal acetylene, 4-(benzyloxy)-1-butyne (5), to give the intermediate titanacyclopentadiene (6) which, upon hydrolysis, deuteriolysis, or iodinolysis, gave diene 8, or its bis-deuterated (>99% d2) and bis-iodinated counterparts (9… Expand
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