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Synlett 2012(4): 541-544  
DOI: 10.1055/s-0031-1290327
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Conversion of Ribose and Other Protected Carbohydrate Derivatives into 2-Deoxy-lactones

Sebastian Wendeborn*, Régis Mondière, Isabelle Keller, Hannes Nussbaumer
Syngenta Crop Protection AG, Werk Stein, Schaffhauserstr., 4332 Stein, Switzerland
Fax: +41(62)8660860; e-Mail: sebastian.wendeborn@syngenta.com;
Further Information

Publication History

Received 31 October 2011
Publication Date:
27 January 2012 (online)

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Abstract

We report the simultaneous reduction of the 2-position and oxidation of the anomeric position in several protected furanosyl and pyranosyl sugar derivatives, mediated through NHC catalysis. This reaction allows the one-step access to highly valuable 2-deoxy-sugars from abundant 2-oxygenated sugar derivatives.

Key words

carbenes - deoxygenation - green chemistry - isomerization - umpolung

    References and Notes

  • 1 De Mesmaeker A. Lebreton J. Jouanno C. Fritsch V. Wolf RM. Wendeborn S. Synlett  1997,  1287 
    Google Scholar
  • 2 Wendeborn S. Jouanno C. Wolf RM. De Mesmaeker A. Tetrahedron Lett.  1996,  37:  5511 
    Google Scholar
  • 3 Wendeborn S. Wolf RM. De Mesmaeker A. Tetrahedron Lett.  1995,  36:  6879 
    Google Scholar
  • 4 Enders D. Niemeier O. Henseler A. Chem. Rev.  2007,  107:  5606 
    Google Scholar
  • 5 Marion N. Díez-González S. Nolan SP. Angew. Chem. Int. Ed.  2007,  46:  2988 
    Google Scholar
  • 6 Vora HU. Rovis T. Aldrichimica Acta  2011,  44:  3 
    Google Scholar
  • 7 Nair V. Menon RS. Biju AT. Sinu CR. Paul RR. Jose A. Sreekumarc V. Chem. Soc. Rev.  2011,  40:  5336 
    Google Scholar
  • 8 Biju AT. Kuhl N. Glorius F. Acc. Chem. Res.  2011,  44:  1182 
    Google Scholar
  • 9 Breslow R. J. Am. Chem. Soc.  1958,  80:  3719 
    Google Scholar
  • 10a Barton DHR. Motherwell WB. Pure Appl. Chem.  1981,  53:  15 
    Google Scholar
  • 10b Barton DHR. Jaszberenyi JC. Tetrahedron Lett.  1989,  30:  2619 
    Google Scholar
  • 11 Chow KY.-K. Bode JW. J. Am. Chem. Soc.  2004,  126:  8126 
    Google Scholar
  • 12 Reynolds NT. Read de Alaniz J. Rovis T. J. Am. Chem. Soc.  2004,  126:  9518 
    Google Scholar
  • 13 Thai K. Li W. Dudding T. Bilodeau F. Gravel M. Org. Lett.  2010,  12:  5708 
    Google Scholar
  • 14 Kim Y.-J. Streitwieser A. J. Am. Chem. Soc.  2002,  124:  5757 
    Google Scholar
  • 15 For calculated pK a of NHC, see: Magill AM. Cavell KJ. Yates BF. J. Am. Chem. Soc.  2004,  126:  8717 
    Google Scholar
  • 16 For a review on characteristics of NHC, see: Dröge T. Glorius F. Angew. Chem. Int. Ed.  2010,  49:  6940 
    Google Scholar
  • 17a

    Spectroscopic Data for Compound 17
    ¹H NMR (400 MHz, DMSO-d 6): δ = 2.22 (dd, J = 17.61, 2.20 Hz, 1 H), 2.81 (dd, J = 17.79, 6.42 Hz, 1 H), 3.47-3.62 (m, 2 H), 4.21-4.32 (m, 2 H), 5.06 (t, J = 5.50 Hz, 1 H), 5.49 (d, J = 4.03 Hz, 1 H).

  • 17b Compound 17 isolated from the NHC-catalyzed rearrangement was identical to that of an authentic sample purchased from Carbosynth (www.carbosynth.com; catalog number MD00127) and to spectral data reported in: Miranda PO. Estévez F. Quintana J. García CI. Brouard I. Padrón JI. Pivel JP. Bermejo J. J. Med. Chem.  2004,  47:  292 
    Google Scholar
  • 18 Grasa GA. Güveli T. Singh R. Nolan SP. J. Org. Chem.  2003,  68:  2812 
    Google Scholar