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Synthesis 2010(21): 3663-3669  
DOI: 10.1055/s-0030-1258213
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Yb(OTf)3-Promoted ZnCl2-Catalyzed Conia-Ene Reaction of Linear β-Alkynic β-Dicarbonyls

Yu Liu, Ren-Jie Song, Jin-Heng Li*
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)88872101; e-Mail: jhli@hunnu.edu.cn;
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Publication History

Received 25 June 2010
Publication Date:
13 August 2010 (online)

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Abstract

An atom-economical and solvent-free ytterbium(III) triflate promoted, zinc(II) chloride catalyzed Conia-ene method has been developed for the construction of five- to six-membered-ring carbocycles. In the presence of zinc(II) chloride and ytterbium(III) triflate, a variety of linear β-alkynic β-keto esters and β-alkynic β-diketones were cyclized under neat conditions in moderate to good yields. It is noteworthy that the selectivity toward five- or six-membered­-ring carbocycles depends on substituents at the terminal alkynes.

Key words

zinc(II) chloride - ytterbium(III) triflate - Conia-ene reaction - linear β-alkynic β-dicarbonyl - carbocycle

    References

  • 1 Caine D. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon Press; New York: 1991.  p.1-63  
    Google Scholar
  • Pd:
  • 2a Corkey BK. Toste FD. J. Am. Chem. Soc.  2005,  127:  17168 
    Google Scholar
  • 2b Lomberget T. Bouyssi D. Balme G. Synthesis  2005,  311 
    Google Scholar
  • 2c Fournet G. Balme G. Van Hemelryck B. Gore J. Tetrahedron Lett.  1990,  31:  5147 
    Google Scholar
  • 2d Fournet G. Balme G. Gore J. Tetrahedron  1991,  47:  6293 
    Google Scholar
  • 2e Balme G. Bouyssi D. Faure R. Gore J. Van Hemelryck B. Tetrahedron  1992,  48:  3891 
    Google Scholar
  • 2f Monteiro N. Gore J. Balme G. Tetrahedron  1992,  48:  10103 
    Google Scholar
  • Mo:
  • 2g McDonald FE. Olson TC. Tetrahedron Lett.  1997,  38:  7691 
    Google Scholar
  • Cu:
  • 2h Bouyssi D. Monteiro N. Balme G. Tetrahedron Lett.  1999,  40:  1297 
    Google Scholar
  • 2i Perez-Hernandez N. Febles M. Perez C. Perez R. Rodriguez ML. Foces-Foces C. Martin JD. J. Org. Chem.  2006,  71:  1139 
    Google Scholar
  • Ti:
  • 2j Kitagawa O. Suzuki T. Inoue T. Watanabe Y. Taguchi T. J. Org. Chem.  1998,  63:  9470 
    Google Scholar
  • Hg:
  • 2k Boaventura MA. Conia JM. Synthesis  1983,  801 
    Google Scholar
  • For papers on Lewis acid mediated reactions, see, for Ti or Zn (an example):
  • 3a Kitagawa O. Suzuki T. Inoue T. Watanabe Y. Taguchi T. J. Org. Chem.  1998,  63:  9470 
    Google Scholar
  • Sn:
  • 3b Kitagawa O. Fujiwara H. Suzuki T. Taguchi T. Shiro M. J. Org. Chem.  2000,  65:  6819 
    Google Scholar
  • Au:
  • 4a Yang S. Ferrali A. Sladojevich F. Campbell L. Dixon DJ. J. Am. Chem. Soc.  2009,  131:  9140 
    Google Scholar
  • 4b Kennedy-Smith JJ. Staben ST. Toste FD. J. Am. Chem. Soc.  2004,  126:  4526 
    Google Scholar
  • 4c Staben ST. Kennedy-Smith JJ. Toste FD. Angew. Chem. Int. Ed.  2004,  43:  5350 
    Google Scholar
  • 4d Mezailles N. Ricard L. Gagosz F. Org. Lett.  2005,  7:  4133 
    Google Scholar
  • 4e Ochida A. Ito H. Sawamura M. J. Am. Chem. Soc.  2006,  128:  16486 
    Google Scholar
  • 4f Pan J.-H. Yang M. Gao Q. Zhu N.-Y. Yang D. Synthesis  2007,  2539 
    Google Scholar
  • 4g Ito H. Makida Y. Ochida A. Ohmiya H. Sawamura M. Org. Lett.  2008,  10:  5051 
    Google Scholar
  • 4h Kuninobu Y. Kawata A. Takai K. Org. Lett.  2005,  7:  4823 
    Google Scholar
  • 5 Ni: Gao Q. Zheng B.-F. Li J.-H. Yang D. Org. Lett.  2005,  7:  2185 
    Google Scholar
  • In:
  • 6a Tsuji H. Yamagata K.-i. Itoh Y. Endo K. Nakamura M. Nakamura E. Angew. Chem. Int. Ed.  2007,  46:  8060 
    Google Scholar
  • 6b Itoh Y. Tsuji H. Yamagata K.-i. Endo K. Tanaka I. Nakamura M. Nakamura E. J. Am. Chem. Soc.  2008,  130:  17161 
    Google Scholar
  • 6c Takahashi K. Midori M. Kawano K. Ishihara J. Hatakeyama S. Angew. Chem. Int. Ed.  2008,  47:  6244 
    Google Scholar
  • Cu/Ag:
  • 7a Deng C.-L. Song R.-J. Guo S.-M. Wang Z.-Q. Li J.-H. Org. Lett.  2007,  9:  5111 
    Google Scholar
  • 7b Deng C.-L. Zou T. Wang Z.-Q. Song R.-J. Li J.-H. J. Org. Chem.  2009,  74:  412 
    Google Scholar
  • 7c Yang T. Ferrali A. Sladojevich F. Campbell L. Dixon DJ. J. Am. Chem. Soc.  2009,  131:  9140 
    Google Scholar
  • 8 Deng C.-L. Song R.-J. Liu Y.-L. Li J.-H. Adv. Synth. Catal.  2009,  351:  3096 
    Google Scholar
  • 9 Snider BB. Merritt JE. Dombroski MA. Buckman BO. J. Org. Chem.  1991,  56:  5544 
    Google Scholar
  • 10 Crimmins MT. Mascarella SW. DeLoach JA. J. Org. Chem.  1984,  49:  3033 
    CrossrefGoogle Scholar
  • 11 D’Ascoli R. D’Auria M. Iavarone C. Piancatelli G. Scettri A. J. Org. Chem.  1980,  45:  4502 
    CrossrefGoogle Scholar
  • 12 Pei T. Wang X. Widenhoefer RA. J. Am. Chem. Soc.  2003,  125:  648 
    CrossrefGoogle Scholar