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Synlett 2010(16): 2415-2420  
DOI: 10.1055/s-0030-1258556
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rapid and Regioselective Hydrogenation of α,β-Unsaturated Ketones and Alkylidene Malonic Diesters Using Hantzsch Ester Catalyzed by Titanium Tetrachloride

Jun Che, Yulin Lam*
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543
Fax: +6567791691; e-Mail: chmlamyl@nus.edu.sg;
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Publikationsverlauf

Received 2 July 2010
Publikationsdatum:
03. September 2010 (online)

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Abstract

A regioselective hydrogenation of α,β-unsaturated ketones and alkylidene malonic diesters using Hantzsch ester as the reducing agent and titanium tetrachloride as a catalyst is described. The short reaction times and mild reaction conditions are the advantages of this method.

Key words

hydrogen transfer - reduction - α,β-unsaturated ketone - alkylidene malonic diester - titanium tetrachloride

    References

  • 1a Moritani Y. Appella DH. Jurkauskas V. Buchwald SL. J. Am. Chem. Soc.  2000,  122:  6797 
    Google Scholar
  • 1b Knowles WS. Angew. Chem. Int. Ed.  2002,  41:  1998 
    Google Scholar
  • 1c Jurkauskas V. Sadighi JP. Buchwald SL. Org. Lett.  2003,  5:  2417 
    Google Scholar
  • 1d Lipshutz BH. Servesko JM. Petersen TB. Papa PP. Lover AA. Org. Lett.  2004,  6:  1273 
    Google Scholar
  • 2a Yoon NM. Pure Appl. Chem.  1996,  68:  843 
    Google Scholar
  • 2b Brown HC. Tetrahedron  1979,  35:  567 
    Google Scholar
  • 3a Murakami Y. Kikuchi J.-I. Hisaeda Y. Hayashida O. Chem. Rev.  1996,  96:  721 
    Google Scholar
  • 3b Stout DM. Meyers AI. Chem. Rev.  1982,  82:  223 
    Google Scholar
  • 3c Eisner U. Kuthan J. Chem. Rev.  1972,  72:  1 
    Google Scholar
  • 3d Garden SJ. Guimarães CRW. Corréa MB. de Oliveira CAF. Pinto AC. Alencastro RB. J. Org. Chem.  2003,  68:  8815 
    Google Scholar
  • 3e Zhu X.-Q. Wang H.-Y. Wang J.-S. Liu Y.-C. J. Org. Chem.  2001,  66:  344 
    Google Scholar
  • 4a You S.-L. Chem. Asian J.  2007,  2:  820 
    Google Scholar
  • 4b Fujii M. Nakamura K. Yasui S. Oka S. Ohno A. Bull. Chem. Soc. Jpn.  1987,  60:  2423 
    Google Scholar
  • 4c Liu Q. Li J. Shen X.-X. Xing R.-G. Yang J. Liu Z. Zhou B. Tetrahedron Lett.  2009,  50:  1026 
    Google Scholar
  • 4d Nakamura K. Fujii M. Ohno A. Oka S. Tetrahedron Lett.  1984,  25:  3983 
    Google Scholar
  • 4e Yasui S. Fujii M. Nakamura K. Ohno A. Bull. Chem. Soc. Jpn.  1987,  60:  963 
    Google Scholar
  • 4f Inoue Y. Imaizumi S. Itoh H. Shinya T. Hashimoto H. Miyano S. Bull. Chem. Soc. Jpn.  1988,  61:  3020 
    Google Scholar
  • 4g Ouellet SG. Walji AM. Macmillan DWC. Acc. Chem. Res.  2007,  40:  1327 
    Google Scholar
  • 4h Barbe G. Charette AB. J. Am. Chem. Soc.  2008,  130:  18 
    Google Scholar
  • 5 He R. Toy PH. La Y. Adv. Synth. Catal.  2008,  350:  54 
    CrossrefGoogle Scholar
  • 6a Fujii M. Aida T. Yoshihara M. Ohno A. Bull. Chem. Soc. Jpn.  1990,  63:  1255 
    Google Scholar
  • 6b Yasui S. Fujii M. Ohno A. Bull. Chem. Soc. Jpn.  1987,  60:  4019 
    Google Scholar
  • 6c Xu H.-J. Liu Y.-C. Fu Y. Chin. J. Chem.  2008,  26:  599 
    Google Scholar
  • 7 Shinkai S. Kusano Y. Ide T. Sone T. Manabe O. Bull. Chem. Soc. Jpn.  1978,  51:  3544 
    CrossrefGoogle Scholar
  • 8 Xu H.-J. Deng G. Yu Q. J. Chem. Soc., Chem. Commun.  1987,  916 
    CrossrefGoogle Scholar