Download PDF
Synlett 2001; 2001(3): 0322-0328
DOI: 10.1055/s-2001-11383
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >