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Synthesis 2011(15): 2459-2465  
DOI: 10.1055/s-0030-1260096
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Functionalized Cyclopropane Derivatives via α-Thiocyanate Ketone-Based Three-Component Reaction

Fei-Yue Wu, Ying Li, Hui Feng, Qiong Wu, Bo Jiang*, Feng Shi, Shu-Jiang Tu*
School of Chemistry and Chemical Engineering, Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu, 221116, P. R. of China
Fax: +86(516)83500065; e-Mail: jiangchem@xznu.edu.cn; e-Mail: laotu@xznu.edu.cn;
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Publication History

Received 30 March 2011
Publication Date:
08 July 2011 (online)

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Abstract

α-Thiocyanate ketone-based three-component reactions have been established for the stereoselective synthesis of functionalized electron-deficient trans-cyclopropanes. The multicomponent reactions were conducted by reacting readily available and inexpensive starting materials under microwave irradiation. The procedures are very facile, highly stereoselective, and avoids the use of ylides.

Key words

multicomponent reactions - cyclopropanes - stereoselectivity - microwave heating

    References

  • 1a de Meijere A. Kozhushkov SI. Khlebnivow AF. Top. Curr. Chem.  2000,  207:  89 
    Google Scholar
  • 1b de Meijere A. Kozhushkov SI. Hadjiarapoglou LP. Top. Curr. Chem.  2000,  207:  149 
    Google Scholar
  • 1c Lysenko IL. Lee HG. Cha JK. Org. Lett.  2006,  8:  2671 
    Google Scholar
  • 2a Djerassi C. Doss GA. New J. Chem.  1990,  14:  713 
    Google Scholar
  • 2b Salaun J. Curr. Med. Chem.  1995,  2:  511 
    Google Scholar
  • 2c Salaun J. Top. Curr. Chem.  2000,  207:  1 
    Google Scholar
  • 2d Faust R. Angew. Chem. Int. Ed.  2001,  40:  2251 
    Google Scholar
  • 3a Lebel H. Marcoux J.-F. Molinaro C. Charette AB. Chem. Rev.  2003,  103:  977 
    Google Scholar
  • 3b Donaldson WA. Tetrahedron  2001,  57:  8589 
    Google Scholar
  • 3c Wessjohan LA. Brandt W. Thiemann T. Chem. Rev.  2003,  103:  1625 
    Google Scholar
  • 3d Reissig HU. Angew. Chem., Int. Ed. Engl.  1996,  35:  971 
    Google Scholar
  • 4a Salaun J. Chem. Rev.  1989,  89:  1247 
    Google Scholar
  • 4b Hartley RC. Caldwell ST. J. Chem. Soc., Perkin Trans. 1  2000,  477 
    Google Scholar
  • 4c Lautens M. Klute W. Tam W. Chem. Rev.  1996,  96:  49 
    Google Scholar
  • 5a Hoveyda AH. Evans DA. Fu GC. Chem. Rev.  1993,  93:  1307 
    Google Scholar
  • 5b Nicolas I. Le Maux P. Simonneaux G. Coord. Chem. Rev.  2008,  252:  727 
    Google Scholar
  • 6 Pellissier H. Tetrahedron  2008,  64:  7041 
    Google Scholar
  • 7a Sun XL. Tang Y. Acc. Chem. Res.  2008,  41:  937 
    Google Scholar
  • 7b Peppe C. das Chagas RP. Burrow RA. J. Organomet. Chem.  2008,  693:  3441 
    Google Scholar
  • 7c Ren ZJ. Cao WG. Ding WY. Wang Y. Wang LL. Synth. Commun.  2004,  34:  3785 
    Google Scholar
  • 8a Ding W.-Y. Han Z.-H. Chen Y.-L. Zou Y.-J. Liu X. Chem. Res. Chin. Univ.  1996,  12:  50 ; Chem. Abstr. 1996, 125, 142141
    Google Scholar
  • 8b Wang Q.-F. Song X.-K. Chen J. Yan C.-G. J. Comb. Chem.  2009,  11:  1007 
    Google Scholar
  • 8c Ren Z.-J. Cao W.-G. Chen J. Wang Y. Ding W.-Y. Synth. Commun.  2005,  35:  3099 
    Google Scholar
  • 8d Peppe C. Pavao das Chagas R. Burrow RA. J. Organomet. Chem.  2008,  693:  3441 
    Google Scholar
  • 8e Zimmerman HE. Binkley RW. Tetrahedron Lett.  1985,  26:  5859 
    Google Scholar
  • 9a Arai S. Nakayama K. Hatano K. Shioiri T. J. Org. Chem.  1998,  63:  9572 
    Google Scholar
  • 9b Arai S. Suzuki Y. Nakayarna K. Hatano K. Shioiri T. Tetrahedron Lett.  1998,  39:  9739 
    Google Scholar
  • 10a Cao W. Zhang H. Chen J. Deng H. Shao M. Lei L. Qian J. Zhu Y. Tetrahedron  2008,  64:  6670 
    Google Scholar
  • 10b Shchepin VV. Stepanyan YuG. Silaichev PS. Vakhrin MI. Russ. J. Gen. Chem.  2006,  76:  1604 
    Google Scholar
  • 10c Kojima S. Suzuki M. Watanabe A. Ohkata K. Tetrahedron Lett.  2006,  47:  9061 
    Google Scholar
  • 11a Pu J.-Q. Jiang H.-Z. Chen X. Qiu M.-Y. Ding W.-Y. Hecheng Huaxue  2000,  8:  356 ; Chem. Abstr. 2000, 134, 178514
    Google Scholar
  • 11b Cao W. Ding W. Chen Y. Gao J. Synth. Commun.  2000,  30:  4523 
    Google Scholar
  • 11c Ren Z.-J. Cao W.-G. Ding W.-Y. Wang Y. Synthesis  2005,  2718 
    Google Scholar
  • 12a Jiang B. Tu S.-J. Kaur P. Wever W. Li G. J. Am. Chem. Soc.  2009,  131:  11660 
    Google Scholar
  • 12b Jiang B. Li C. Shi F. Tu S.-J. Kaur P. Wever W. Li G. J. Org. Chem.  2010,  75:  2962 
    Google Scholar
  • 12c Ma N. Jiang B. Zhang G. Tu S.-J. Wever W. Li G. Green Chem.  2010,  12:  1357 
    Google Scholar
  • 13a Tu SJ. Jiang B. Jia RH. Zhang JY. Zhang Y. Yao CS. Shi F. Org. Biomol. Chem.  2006,  4:  3664 
    Google Scholar
  • 13b Tu S.-J. Cao X.-D. Hao W.-J. Zhang X.-H. Yan S. Wu S.-S. Han Z.-G. Shi F. Org. Biomol. Chem.  2009,  7:  557 
    Google Scholar
  • 13c Jiang B. Hao W.-J. Zhang J.-P. Tu S.-J. Shi F. Org. Biomol. Chem.  2009,  7:  1171 
    Google Scholar
  • 13d Jiang B. Hao W.-J. Zhang J.-P. Tu S.-J. Shi F. Org. Biomol. Chem.  2009,  7:  2195 
    Google Scholar
  • 13e Jiang B. Cao L.-J. Tu S.-J. Zheng W.-R. Yu H.-Z. J. Comb. Chem.  2009,  11:  612 
    Google Scholar
  • 14a Bisogno FR. Cuetos A. Green Chem.  2009,  11:  452 
    Google Scholar
  • 14b El-Din AS. Sulfur Lett.  2003,  26:  35 
    Google Scholar
15

Single-crystal growth was carried out in ethanol at room temperature. X-ray crystallographic analysis was performed with a Siemens SMART CCD and a Siemens P4 diffractometer (graphite monochromator, MoKα radiation λ = 0.71073 Å). Crystal data for 6a: Empirical formula: C18H11BrN2O; formula weight: 351.20; crystal dimensions 0.48 × 0.40 × 0.30 mm; triclinic; space group P1; a = 8.0590(10) Å, b = 10.3631(12) Å, c = 11.2581(13) Å, α = 63.9500(10)˚, β = 69.676(2)˚, γ = 67.348(2)˚; µ = 2.702 mm-¹; V = 761.34(16) ų; Z = 2; D(calcd) = 1.532 Mg/m³; F(000) = 352, S = 1.058, R 1 = 0.0526, wR 2 = 0.1288