Download PDF
Synthesis 2010(5): 844-848  
DOI: 10.1055/s-0029-1218590
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First TDAE-Mediated Double Addition of Nitrobenzylic Anions to Aromatic Dialdehydes

Thierry Juspin, Gamal Giuglio-Tonolo, Thierry Terme, Patrice Vanelle*
Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Universités d’Aix-Marseille I, II et III - CNRS, UMR 6264, Laboratoire Chimie Provence, 27 Boulevard J. Moulin, 13385 Marseille Cedex 05, France
Fax: +33(4)91794677; e-Mail: patrice.vanelle@pharmacie.univ-mrs.fr;
Further Information

Publication History

Received 19 October 2009
Publication Date:
07 December 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

We report herein the first tetrakis(dimethylamino)ethylene (TDAE)-mediated double addition of nitrobenzylic anions to aromatic dialdehydes such as terephthalaldehyde and isophthalaldehyde, and have developed a new methodology that allows us to observe the double addition. This TDAE-mediated approach is an original and mild method with which to generate tri-aromatic diols.

Key words

TDAE - dialdehydes - reduction - nucleophilic addition - nitrobenzyl anions

    References

  • 1 Pruett RL. Barr JT. Rapp KE. Bahner CT. Gibson JD. Lafferty RH. J. Am. Chem. Soc.  1950,  72:  3646 
    CrossrefGoogle Scholar
  • 2 Carpenter W. J. Org. Chem.  1966,  31:  789 
    CrossrefGoogle Scholar
  • 3a Pawelke G. J. Fluorine Chem.  1989,  42:  429 
    Google Scholar
  • 3b Pawelke G. J. Fluorine Chem.  1991,  52:  229 
    Google Scholar
  • 4 Burkholder C. Dolbier WR. Médebielle M. J. Org. Chem.  1998,  63:  5385 
    CrossrefGoogle Scholar
  • 5 Xu W. Dolbier RW. J. Org. Chem.  2005,  70:  4741 
    CrossrefGoogle Scholar
  • 6a Nishiyama Y. Kabawata H. Kobayashi A. Nishino T. Sonida N. Tetrahedron Lett.  2005,  46:  867 
    Google Scholar
  • 6b Nishiyama Y. Kawabata H. Tetrahedron Lett.  2006,  47:  5565 
    Google Scholar
  • 7 Kuroboshi M. Tanaka M. Kishimoto S. Goto K. Mochisuki M. Tanaka H. Tetrahedron Lett.  2000,  41:  81 
    CrossrefGoogle Scholar
  • 8a Kuroboshi M. Waki Y. Tanaka H. Synlett  2002,  637 
    Google Scholar
  • 8b Kuroboshi M. Waki Y. Tanaka H. J. Org. Chem.  2003,  68:  3938 
    Google Scholar
  • 8c Park SB. Alper H. Tetrahedron Lett.  2004,  45:  5515 
    Google Scholar
  • 9a Murphy JA. Khan TA. Zhou S. Thomson DW. Mahesh M. Angew. Chem. Int. Ed.  2005,  44:  1356 
    Google Scholar
  • 9b Murphy JA. Zhou S. Thomson DW. Schoenebeck F. Mahesh M. Park SR. Tuttle T. Berlouis LEA. Angew. Chem. Int. Ed.  2007,  46:  5178 
    Google Scholar
  • 9c Schoenebeck F. Murphy JA. Zhou S. Uenoyama Y. Miclo Y. Tuttle T. J. Am. Chem. Soc.  2007,  129:  13368 
    Google Scholar
  • 9d Garnier J. Murphy JA. Zhou SZ. Turner AT. Synlett  2008,  2127 
    Google Scholar
  • 9e Cutulic SPY. Murphy JA. Farwaha H. Zhou SZ. Chrystal E. Synlett  2008,  2132 
    Google Scholar
  • 9f Murphy JA. Garnier J. Park SR. Schoenebeck F. Zhou S. Turner AT. Org. Lett.  2008,  10:  1227 
    Google Scholar
  • 9g Mahesh M. Murphy JA. LeStrat F. Wessel HP. Beilstein J. Org. Chem.  2009,  5 
    Google Scholar
  • 10 Burkholder C. Dolbier WR. Médebielle M. J. Fluorine Chem.  2001,  109:  39 
    Google Scholar
  • 11a Burkholder C. Dolbier WR. Médebielle M. J. Org. Chem.  1998,  63:  5385 
    Google Scholar
  • 11b Ait-Mohand S. Takechi N. Médebielle M. Dolbier WR. Org. Lett.  2001,  3:  4271 
    Google Scholar
  • 11c Médebielle M. Keirouz R. Okada E. Ashida T. Synlett  2001,  821 
    Google Scholar
  • 11d Dolbier WR. Médebielle M. Ait-Mohand S. Tetrahedron Lett.  2001,  42:  4811 
    Google Scholar
  • 11e Takechi N. Ait-Mohand S. Médebielle M. Dolbier WR. Tetrahedron Lett.  2002,  43:  4317 
    Google Scholar
  • 12a Giuglio-Tonolo G. Terme T. Médebielle M. Vanelle P. Tetrahedron Lett.  2003,  44:  6433 
    Google Scholar
  • 12b Giuglio-Tonolo G. Terme T. Médebielle M. Vanelle P. Tetrahedron Lett.  2004,  45:  5121 
    Google Scholar
  • 12c Giuglio-Tonolo G. Terme T. Vanelle P. Synlett  2005,  251 
    Google Scholar
  • 12d Amiri-Attou O. Terme T. Vanelle P. Synlett  2005,  3047 
    Google Scholar
  • 12e Amiri-Attou O. Terme T. Vanelle P. Molecules  2005,  10:  545 
    Google Scholar
  • 12f Montana M. Terme T. Vanelle P. Tetrahedron Lett.  2005,  46:  8373 
    Google Scholar
  • 12g Montana M. Terme T. Vanelle P. Tetrahedron Lett.  2006,  47:  6573 
    Google Scholar
  • 12h Amiri-Attou O. Terme T. Médebielle M. Vanelle P. Tetrahedron Lett.  2008,  49:  1016 
    Google Scholar
  • 12i Khoumeri O. Montana M. Terme T. Vanelle P. Tetrahedron  2008,  64:  11237 
    Google Scholar
  • 12j Montana M. Crozet MD. Castera-Ducros C. Terme T. Vanelle P. Heterocycles  2008,  75:  925 
    Google Scholar
  • 12k Juspin T. Terme T. Vanelle P. Synlett  2009,  1485 
    Google Scholar
  • 13 Andrieux CP. Gallardo I. Savéant JM. Su K.-B. J. Am. Chem. Soc.  1986,  108:  638 
    CrossrefGoogle Scholar