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Synthesis and Rearrangement of Silylated Oxy-Cope Systems

Addition of allyl or vinyl organometallic reagents to chiral a,b- or b,g-unsaturated acylsilanes afforded stereoselectively 3-silylated 3-hydroxy-1,5-dienes that are stereoselectively converted to d,e-unsaturated acylsilanes by the thermal oxy-Cope rearrangement. The rearrangement is restricted to compounds possessing an (alkoxy)methyl substituent at the silicon moiety; upon heating, analogous compounds with the t-BuMe2Si group in the 3-position led to decomposition only. The (alkoxy)methyl group at silicon is supposed to act as a weak internal base, which accelerates the rearrangment reaction.

  • Content Type Journal Article
  • Pages 9-19
  • DOI 10.1007/s007830050071
  • Authors
    • P. Koch-Huber, Institute of Organic Chemistry, University of Zurich, Winterthurerstr. 190, CH-8057 Zurich. E-mail: sbienz@oci.unizh.ch
    • R.W. Kunz, Institute of Organic Chemistry, University of Zurich, Winterthurerstr. 190, CH-8057 Zurich. E-mail: sbienz@oci.unizh.ch
    • S. Bienz, Institute of Organic Chemistry, University of Zurich, Winterthurerstr. 190, CH-8057 Zurich. E-mail: sbienz@oci.unizh.ch
    • Journal Molecules Online
    • Online ISSN 1433-1373
    • Journal Volume Volume 3
    • Journal Issue Volume 3, Number 2

Authors:   P. Koch-Huber, R.W. Kunz, S. Bienz
Journal:   Molecules Online
Year:   2004
DOI:   10.1007/s007830050071
Publication date:   19-Feb-2004
Facts, background information, dossiers
  • reagents
  • Oxy-Cope Rearrangement
  • Cope Rearrangement
More about Springer-Verlag
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