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Synlett 2001; 2001(3): 0322-0328
DOI: 10.1055/s-2001-11383
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Stereospecific or Stereoselective Elimination of vicinal-Alkoxyiodoalkanes by Means of Organometallic Reagents

Hiroshi Shinokubo* , Koichiro Oshima
  • *Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan; Fax + 81-75-753-48 63; E-mail: oshima@fm1.kuic.kyoto-u.ac.jp
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Publikationsdatum:
31. Dezember 2001 (online)

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Stereospecific or stereoselective elimination reactions of vicinal alkoxyiodoalkanes provide both stereo- and regiochemically defined alkenes via organometallic reagents. Three different reaction conditions have been developed. The first is the organolithium-induced stereospecific syn-elimination of a β-methoxy alkyl iodide. This method can be successfully applied to the interconversion of olefinic geometrical isomers. The second is a stereoselective elimination using a Grignard reagent. An isomeric mixture of alkenes can be converted into a pure (E)-alkene by this method. Finally, allylsilane/TiCl4-mediated stereospecific anti-elimination of iodoalkoxyalkanes is described. These methods provide new routes for the stereoselective synthesis of alkenes. Stereoselective synthesis of the substrates is also discussed.

alkenes - eliminations - isomerizations - organometallic reagents - stereoselective synthesis