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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

    References

  • 1 Claisen L. Chem. Ber.  1912,  45:  3157 
    Search in Google Scholar
  • For selected reviews of [3,3]-sigmatropic rearrangement, see:
  • 2a Lutz RR. Chem. Rev.  1984,  84:  205 
    Search in Google Scholar
  • 2b Ziegler FE. Chem. Rev.  1988,  88:  1423 
    Search in Google Scholar
  • 2c Davies HML. Tetrahedron  1993,  49:  5203 
    Search in Google Scholar
  • 2d Paquette LA. Tetrahedron  1997,  53:  13971 
    Search in Google Scholar
  • 2e Hiersemann M. Abraham L. Eur. J. Org. Chem.  2002,  1461 
  • 2f Nubbemeyer U. Synthesis  2003,  961 
  • 2g Majumdar KC. Alam S. Chattopadhyay B. Tetrahedron  2008,  64:  597 
    Search in Google Scholar
  • 2h Castro AMM. Chem. Rev.  2004,  104:  2939 
    Search in Google Scholar
  • 2i The Claisen Rearrangement   Hiersemann M. Nubbemeyer U. Wiley-VCH; Weinheim: 2007. 
  • 3 For a recent review, see: de la Pradilla RF. Tortosa M. Viso A. Top. Curr. Chem.  2007,  275:  103 
    Search in Google Scholar
  • 4 For charge-accelerated Claisen rearrangements, see: Madelaine C. Valerio V. Maulide N. Angew. Chem. Int. Ed.  2010,  49:  1583 ; and references therein
    Search in Google Scholar
  • 5a Trost BM. Melvin LS. Sulfur Ylides   Academic Press; New York: 1975. 
  • 5b Li A.-H. Dai L.-X. Aggarwal VK. Chem. Rev.  1997,  97:  2341 
    Search in Google Scholar
  • 5c Aggarwal VK. Winn CL. Acc. Chem. Res.  2004,  37:  611 
    Search in Google Scholar
  • 5d Tang Y. Ye S. Sun X.-L. Synlett  2005,  2720 
  • 5e McGarrigle EM. Meyers EL. Illa O. Shaw MA. Riches SL. Aggarwal VK. Chem. Rev.  2007,  107:  5841 
    Search in Google Scholar
  • 5f Topics in Current Chemistry   Vols. 274 and 275:  Springer; Berlin: 2007. 
  • 6a For selected review on sulfur-mediated [2,3]-sigmatropic rearrangements, see: Topics in Current Chemistry   Vol. 275:  Springer; Berlin: 2007. 
  • 6b For selected review on sulfur-mediated Belluš-Claisen rearrangements, see: Bonda J. Angew. Chem. Int. Ed.  2004,  43:  3516 
    Search in Google Scholar
  • 6c For aromatic ortho-Claisen rearrangement, see: Majumdar KC. Synlett  2008,  2400 
  • 7 Kennedy AR. Taday MH. Rainier JD. Org. Lett.  2001,  3:  2407 
    Search in Google Scholar
  • 8 Novikov AV. Kennedy AR. Rainier JD. J. Org. Chem.  2003,  68:  993 
    Search in Google Scholar
  • 9 Nyong AM. Rainier JD. J. Org. Chem.  2005,  70:  746 
    Search in Google Scholar
  • 10 Boyarskikh V. Nyong A. Rainier JD. Angew. Chem. Int. Ed.  2008,  47:  5374 
    Search in Google Scholar
  • 11 Sabahi A. Rainier JD. ARKIVOC  2010,  (viii):  116 
    Search in Google Scholar
  • 12a Shapiro ND. Toste FD. J. Am. Chem. Soc.  2007,  129:  4160 
    Search in Google Scholar
  • 12b Li G. Zhang L. Angew. Chem. Int. Ed.  2007,  46:  5156 
    Search in Google Scholar
  • 13 For a recent mini-review on gold α-oxo carbenoids in catalysis, see: Xiao J. Li X. Angew. Chem. Int. Ed.  2011,  50:  7226 
    Search in Google Scholar
  • 14 Cuenca AB. Montserrat S. Hossain KM. Mancha G. Lledós A. Medio-Simón M. Ujaque G. Asensio G. Org. Lett.  2009,  11:  4906 
    Search in Google Scholar
  • 15 Li C.-W. Pati K. Lin G.-Y. Sohel SMdA. Hung H.-H. Liu R.-S. Angew. Chem. Int. Ed.  2010,  49:  9891 
    Search in Google Scholar
  • 16 Yoshida S. Yorimitsu H. Oshima K. Org. Lett.  2009,  11:  2185 
    Search in Google Scholar
  • 17 For recent review on Pummerer reaction, see: Smith LHS. Coote SC. Sneddon HF. Procter DJ. Angew. Chem. Int. Ed.  2010,  49:  5832 
    Search in Google Scholar
  • 18 By ipso-substitution we refer to overall direct substitution of SiR3 by the electrophile, without allylic transposition
  • 19 Kobatake T. Yoshida S. Yorimitsu H. Oshima K. Angew. Chem. Int. Ed.  2010,  49:  2340 
    Search in Google Scholar
  • 20 Kobatake T. Fujino D. Yoshida S. Yorimitsu H. Oshima K. J. Am. Chem. Soc.  2010,  132:  11838 
    Search in Google Scholar
  • 21 Huang X. Maulide N. J. Am. Chem. Soc.  2011,  133:  8510 
    Search in Google Scholar
  • 22 Huang X. Goddard R. Maulide N. Angew. Chem. Int. Ed.  2010,  49:  8979 
    Search in Google Scholar
  • 23a Cook AF. Moffatt JG. J. Am. Chem. Soc.  1968,  90:  740 
    Search in Google Scholar
  • 23b Daves D. Anderson WR. Pickering MV. J. Chem. Soc., Chem. Commun.  1974,  301 
  • 23c Hartke K. Strangemann D. Heterocycles  1986,  24:  2399 
    Search in Google Scholar
  • For selected reviews on Pummerer reactions, see ref. 17 and:
  • 24a Carreño MC. Chem. Rev.  1995,  95:  1717 
    Search in Google Scholar
  • 24b Bur SK. Padwa A. Chem. Rev.  2004,  104:  2401 
    Search in Google Scholar
  • 25 Eberhart AJ. Imbriglio JE. Procter DJ. Org. Lett.  2011,  13:  5882 
    Search in Google Scholar