Download PDF
Synlett 2009(16): 2669-2672  
DOI: 10.1055/s-0029-1217977
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Catalytic Sulfonyloxylactonization of Alkenoic Acids Using Hypervalent Iodine(III) Reagent

Jie Yan*, Hong Wang, Zhenping Yang, Yan He
College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, Zhejiang, P. R. of China
Fax: +86(571)88320238; e-Mail: jieyan87@zjut.edu.cn;
Further Information

Publication History

Received 22 June 2009
Publication Date:
10 September 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel and efficient catalytic method for sulfonyloxylactonization of alkenoic acids is reported. (Diacetoxyiodo)benzene could be used as a recyclable catalyst in combination with m-chloroperbenzoic acid as an oxidant in the presence of sulfonic acid to effect the cyclization of various alkenoic acids in CH2Cl2 at room temperature, giving sulfonyloxylactones in good yields.

Key words

sulfonyloxylactonization - hypervalent iodine reagent - catalytic cyclization

    References and Notes

  • 1a Varvoglis A. Tetrahedron  1997,  53:  1179 
    Google Scholar
  • 1b Stang PJ. Zhdankin VV. Chem. Rev.  1996,  96:  1123 
    Google Scholar
  • 1c Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 
    Google Scholar
  • 1d Kirschning A. Eur. J. Org. Chem.  1998,  11:  2267 
    Google Scholar
  • 1e Ochiai M. J. Organomet. Chem.  2000,  611:  494 
    Google Scholar
  • 1f Okuyama T. Acc. Chem. Res.  2002,  35:  12 
    Google Scholar
  • 1g Zhdankin VV. Stang PJ. Tetrahedron  1998,  54:  10927 
    Google Scholar
  • 1h Grushin VV. Chem. Soc. Rev.  2000,  29:  315 
    Google Scholar
  • 2a Varvoglis A. Hypervalent Iodine in Organic Synthesis   Academic Press; Oxford: 1997. 
    Google Scholar
  • 2b Wirth T. Hirt UH. Synthesis  1999,  1271 
    Google Scholar
  • 2c Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 
    Google Scholar
  • 2d Top. Curr. Chem.   Vol. 224:  Wirth T. Springer; Berlin: 2003. 
    Google Scholar
  • 3a Boye AC. Meyer D. Ingison CK. French AN. Wirth T. Org. Lett.  2003,  5:  2157 
    Google Scholar
  • 3b Shah M. Taschner MJ. Koser GF. Rach NL. Tetrahedron Lett.  1986,  27:  4557 
    Google Scholar
  • 3c Koser GF. Lodaya JS. Ray DG. Kokil PB. J. Am. Chem. Soc.  1988,  110:  2987 
    Google Scholar
  • 4a Dohi T. Kita Y. Kagaku  2006,  61:  68 
    Google Scholar
  • 4b Richardson RD. Wirth T. Angew. Chem. Int. Ed.  2006,  45:  4402 
    Google Scholar
  • 4c Dohi T. Minamitsuji Y. Maruyama A. Hirose S. Kita Y. Org. Lett.  2008,  10:  3559 
    Google Scholar
  • 4d Ochiai M. Chem. Rec.  2007,  7:  13 
    Google Scholar
  • 4e Uyanik M. Ishihara K. Chem. Commun.  2009,  2086 
    Google Scholar
  • 4f Dohi T. Kita Y. Chem. Commun.  2009,  2073 
    Google Scholar
  • 4g Liu H.-G. Tan C.-H. Tetrahedron Lett.  2007,  48:  8220 
    Google Scholar
  • 5a Dohi T. Maruyama A. Yoshimura M. Morimoto K. Tohma H. Kita Y. Angew. Chem. Int. Ed.  2005,  44:  6193 
    Google Scholar
  • 5b Dohi T. Maruyama A. Minamitsuji Y. Takenaga N. Kita Y. Chem. Commun.  2007,  1224 
    Google Scholar
  • 6 Ochiai M. Takeuchi Y. Katayama T. Sueda T. Miyamoto K. J. Am. Chem. Soc.  2005,  127:  12244 
    CrossrefPubMedGoogle Scholar
  • 7a Yamamoto Y. Togo H. Synlett  2006,  798 
    Google Scholar
  • 7b Yamamoto Y. Kawano Y. Toyb PH. Togo H. Tetrahedron  2007,  63:  4680 
    Google Scholar
  • 7c Richardson RD. Page TK. Altermann S. Paradine SM. French AN. Wirth T. Synlett  2007,  538 
    Google Scholar
  • 7d Akiike J. Yamamoto Y. Togo H. Synlett  2007,  2168 
    Google Scholar
  • 7e Altermann SM. Richardson RD. Page TK. Schmidt RK. Holland E. Mohammed U. Paradine SM. French AN. Richter C. Bahar AM. Witulski B. Wirth T. Eur. J. Org. Chem.  2008,  5315 
    Google Scholar
8

Typical Procedure for the Catalytic Sulfonyloxylactonization of Alkenoic Acids
To CH2Cl2 (2 mL), alkenoic acid 1 (0.3 mmol),(diacetoxy-iodo)benzene (0.03 mmol), MCPBA (75%, 0.3 mmol) and sulfonic acid 2 (0.3 mmol) were added. The mixture was stirred at r.t. for 24 hours and then H2O (5 mL), sat. aq Na2S2O3 (2 mL), and sat. aq Na2CO3 (2 mL) were added.
The mixture was extracted with CH2Cl2 (2 × 5 mL), the combined organic layer was washed with brine, dried over anhyd MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC on a silica gel using (hexane-EtOAc, 2:1) as eluent to give sulfonyloxylacton 3 in good yields.