Sulfur Participation in [3,3]-Sigmatropic Rearrangements

  • Roberto Fernández de la Pradilla
  • Mariola Tortosa
  • Alma Viso
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 275)

Abstract

The thio-Claisen rearrangement is a general and facile process that is often advantageous overthe standard Claisen rearrangement. Several asymmetric variants of the thio-Claisen rearrangement havebeen reported. The rearrangement of sulfonium salts and sulfoxides takes place even more readily. Alkenylsulfoxides and sulfilimines undergo a highly stereocontrolled cyclization to lactones and lactams,respectively, upon reaction with haloketenes; this synthetically useful process entails a [3,3]-sigmatropicrearrangement of a zwitterionic intermediate. Sulfur-containing functionalities located at the peripheryof the Claisen substrates exert a powerful influence on the outcome of the process.

Sulfur [3,3]-sigmatropic rearrangements Thio-Claisen Sulfoxides Sulfilimines 

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Notes

Acknowledgments

This article was supported by DGICYT (BQU2003-02921 and CTQ2005-04632). We thank JANSSEN-CILAG for generous additional support. Also, we would like to thank Prof. Meztner for providing a preprint of his manuscript [3].

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Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  • Roberto Fernández de la Pradilla
    • 1
  • Mariola Tortosa
    • 1
  • Alma Viso
    • 1
  1. 1.Instituto de Química Orgánica GeneralConsejo Superior de Investigaciones CientíficasMadridSpain

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