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Synthesis 2012(2): 175-183  
DOI: 10.1055/s-0031-1289632
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Charge-Accelerated Sulfonium [3,3]-Sigmatropic Rearrangements

Xueliang Huang, Sebastian Klimczyk, Nuno Maulide*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062999; e-Mail: maulide@mpi-muelheim.mpg.de;
Further Information

Publication History

Received 6 October 2011
Publication Date:
01 December 2011 (online)

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Abstract

Charge-accelerated sigmatropic rearrangements are useful reactions for the creation of key C-C bonds in synthesis. In this mini-review, recent developments in sulfonium [3,3]-sigmatropic rearrangements that take place under mild and operationally simple conditions are presented and discussed in a unified manner.

1 Introduction

2 Metal-Mediated Sulfonium [3,3]-Sigmatropic Rearrangements

2.1 Rhodium Carbene Promoted Rearrangements

2.2 Gold-Mediated Thio-Claisen Rearrangements

3 Anhydride-Triggered Sulfonium Rearrangement

3.1 Activation of Ketene Dithioacetal Derivatives

3.2 Aryl Sulfoxide Mediated Sulfonium [3,3]-Sigmatropic Rearrangements

4 Conclusions and Outlook

Key words

thio-Claisen rearrangement - cationic sulfur - metal carbene - anhydride - sulfoxides

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