Synlett 2008(13): 1949-1952  
DOI: 10.1055/s-2008-1077967
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

FeCl3/TMSCl: An Effective Catalytic System for the Conjugate Addition of Sodium p-Toluenesulfinate to α,β-Enones

B. Sreedhar*, M. Amarnath Reddy, P. Surendra Reddy
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160921; e-Mail: sreedharb@iict.res.in;
Further Information

Publication History

Received 30 January 2008
Publication Date:
15 July 2008 (online)

Abstract

A new protocol for the β-sulfonation of α,β-unsaturated carbonyl compounds is described. The method employs FeCl3 as catalyst and TMSCl as additive for conjugate addition of sodium p-toluenesulfinate to enones.

    References and Notes

  • 1a Patai ES. Rappoport Z. Stirling C. The Chemistry of Sulphones and Sulphoxides   John Wiley and Sons; Chichester: 1988. 
  • 1b Simpkins NS. Sulphones in Organic Synthesis   Pergamon Press; Oxford: 1993. 
  • 1c Backvall J.-E. Chinchilla R. Najera C. Yus M. Chem. Rev.  1998,  98:  2291 
  • 1d Back TG. Tetrahedron  2001,  57:  5263 
  • 1e Chemla F. J. Chem. Soc., Perkin Trans. 1  2002,  275 
  • 2 Najera C. Sansano JM. Recent Res. Dev. Org. Chem.  1998,  2:  637 
  • 3 Paquette LA. Synlett  2001,  1 
  • 4 Chinchilla R. Najera C. Recent Res. Dev. Org. Chem.  1997,  1:  437 
  • 5 Najera C. Yus M. Tetrahedron  1999,  55:  10547 
  • 6a Krug RC. Rigney JA. Tichelaar GR. J. Org. Chem.  1962,  27:  1305 
  • 6b Burger JJ. Chen TBRA. DeWaard ER. Huisman HO. Tetrahedron  1980,  36:  723 
  • 6c Naf F. Decorzant R. Escher SD. Tetrahedron Lett.  1982,  23:  5043 
  • 6d Solladie G. In Comprehensive Organic Synthesis   Vol. 6:  Trost BM. Fleming I. Pergamon; Oxford: 1991.  p.133-170  ; and references cited therein
  • 6e Crandall JK. Pradat C. J. Org. Chem.  1985,  50:  1327 ; and references cited therein
  • 7 Skarzewski J. Siedlecka R. Wojaczynska E. Zielinska-Blajet M. Tetrahedron: Asymmetry  2002,  13:  2105 
  • 8a Tamura M. Kochi JK. J. Am. Chem. Soc.  1971,  93:  1487 
  • 8b Tamura M. Kochi JK. Synthesis  1971,  303 
  • 8c Tamura M. Kochi JK. J. Organomet. Chem.  1971,  31:  289 
  • 9a Bolm C. Legros J. Le Paih J. Zani L. Chem. Rev.  2004,  104:  6217 ; and references cited therein
  • 9b Sayed AA. Wadia MS. J. Chem. Res., Synop.  2001,  9:  362 
  • 9c Kohler EP. Larsen RG. J. Am. Chem. Soc.  1936,  58:  1518 
  • 10a Xu L.-W. Xia C.-G. Hu X.-X. Chem. Commun.  2003,  2570 
  • 10b Yang L. Xu L.-W. Xia C.-G. Tetrahedron Lett.  2007,  48:  1599