Download PDF
Synthesis 2011(19): 3109-3114  
DOI: 10.1055/s-0030-1260176
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalyzed Synthesis of α-(Substituted Methyl)vinylphosphonates

Cécile Garzon, Mireille Attolini*, Michel Maffei*
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille (iSm2), UMR CNRS 6263, équipe HIT, B.P. 551, Campus scientifique de Saint Jérôme, 13397 Marseille Cedex 20, France
Fax: +33(4)91289402; e-Mail: michel.maffei@univ-cezanne.fr; e-Mail: mireille.attolini@univ-cezanne.fr;
Further Information

Publication History

Received 11 May 2011
Publication Date:
18 August 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

α-(Substituted methyl)vinylphosphonates are obtained by a DABCO-catalyzed substitution reaction of diethyl α-(tert-butoxycarbonyloxymethyl)vinylphosphonate­ and (N-protected) amino- or soft pronucleophiles. The reactions are easily performed under mild conditions (r.t., 1 h), and give good to excellent yields of the title compounds. A diphosphonate by-product was isolated in some examples, when the nucleophile has a less pronounced nucleophilic character.

Key words

α-(substituted methyl)vinylphosphonates - organocatalysis - diethyl α-(tert-butoxycarbonyloxymethyl)vinylphosphonate - pronucleophiles - 1,4-diazabicyclo[2.2.2]octane

    References

  • 1a Minami T. Motoyoshiya J. Synthesis  1992,  333 
    Google Scholar
  • 1b Maffei M. Curr. Org. Synth.  2004,  1:  355 
    Google Scholar
  • 1c Dembitsky VM. Al Quntar AAA. Haj-Yehiaa A. Srebnik M. Mini-Rev. Org. Chem.  2005,  2:  91 
    Google Scholar
  • 2a Krawczyk H. Synth. Commun.  1994,  24:  2263 
    Google Scholar
  • 2b Krawczyk H. Phosphorus, Sulfur Silicon Relat. Elem.  1995,  101:  221 
    Google Scholar
  • 2c Gurevich IE. Tebby JC. J. Chem. Soc., Perkin Trans. 1  1995,  1259 
    Google Scholar
  • 2d Gurevich IE. Tebby JC. Dogadina AV. Ionin BI. Phosphorus, Sulfur Silicon Relat. Elem.  1999,  148:  61 
    Google Scholar
  • 2e Loretto MA. Pompili C. Tardella PA. Tetrahedron  2001,  57:  4423 
    Google Scholar
  • 2f Sergeeva NN. Golubev AS. Hennig L. Burger K. Synthesis  2003,  915 
    Google Scholar
  • 2g Park H. Cho CW. Krische MJ. J. Org. Chem.  2006,  71:  7892 
    Google Scholar
  • 2h Gajda A. Gajda T. Tetrahedron  2008,  64:  1233 
    Google Scholar
  • 2i Rabasso N. Fadel A. Tetrahedron Lett.  2010,  51:  60 
    Google Scholar
  • For reviews on the synthesis and biological activities of β-aminophosphonates, see :
  • 3a Stowasser B. Budt K.-H. Qi LJ. Peyman A. Ruppert D. Tetrahedron Lett.  1992,  33:  6625 
    Google Scholar
  • 3b Wester RT. Chambers RJ. Green MD. Murphy WR. Bioorg. Med. Chem. Lett.  1994,  4:  2005 
    Google Scholar
  • 3c Patel DV. Reilly-Gauvin K. Ryono DE. Free CA. Rogers WL. Smith SA. DeForrest JM. Oehl RS. Petrillo EW. J. Med. Chem.  1995,  38:  4557 
    Google Scholar
  • 3d Zygmunt J. Gancarz R. Lejczak B. Wieczorek P. Kafarski P. Bioorg. Med. Chem. Lett.  1996,  6:  2989 
    Google Scholar
  • 3e Tao M. Bihovsky R. Wells GJ. Mallamo JP. J. Med. Chem.  1998,  41:  3912 
    Google Scholar
  • 3f Aminophosphonic and Aminophosphinic Acids   Kukhar VP. Hudson HR. Wiley; New York: 2000. 
    Google Scholar
  • 3g Palacios F. Alonso C. de Los Santos JM. Chem. Rev.  2005,  105:  899 
    Google Scholar
  • 3h Whitteck JT. Ni W. Griffin BM. Eliot AC. Thomas PM. Kelleher NL. Metcalf WW. van der Donk WA. Angew. Chem. In. Ed. Engl.  2007,  46:  9089 
    Google Scholar
  • 3i Al Quntar AAA. Gallily R. Katzavian G. Srebnik M. Eur. J. Pharm.  2007,  556:  9 
    Google Scholar
  • 4 M’rabet H. M’hamed MO. Efrit ML. Synth. Commun.  2009,  39:  1655 
    CrossrefGoogle Scholar
  • 5 Garzon C. Attolini M. Maffei M. Tetrahedron Lett.  2010,  51:  3772 
    CrossrefGoogle Scholar
  • For selected examples, see :
  • 6a Du Y. Han X. Lu X. Tetrahedron Lett.  2004,  45:  4967 
    Google Scholar
  • 6b Zheng S. Lu X. Org. Lett.  2008,  10:  4481 
    Google Scholar
  • 6c Cui HL. Huang JR. Lei J. Wang ZF. Chen S. Wu S. Chen YC. Org. Lett.  2010,  12:  720 
    Google Scholar
  • 6d Lei J. Cui HL. Li R. Wu L. Ding ZY. Chen YC. Org. Biomol. Chem.  2010,  8:  2840 
    Google Scholar
  • 6e Hong L. Sun W. Liu C. Zhao D. Wang R. Chem. Commun.  2010,  46:  2856 
    Google Scholar
  • 6f Peng J. Huang X. Cui HL. Chen YC. Org. Lett.  2010,  12:  4260 
    Google Scholar
  • 6g Basavaiah D. Reddy BS. Badsara SS. Chem. Rev.  2010,  110:  5447 
    Google Scholar
  • 7 Capuzzi M. Perdicchia D. Jorgensen KA. Chem. Eur. J.  2008,  14:  128 
    CrossrefGoogle Scholar
  • 8 Rambaud M. Del Vecchio A. Villieras J. Synth. Commun.  1984,  14:  833 
    CrossrefGoogle Scholar
  • 9a Taillier C. Hameury T. Bellosta V. Cossy J. Tetrahedron  2007,  63:  4472 
    Google Scholar
  • 9b Feltenberger JB. Hayashi R. Tang Y. Babiash ESC. Hsung RP. Org. Lett.  2009,  11:  3666 
    Google Scholar