Download PDF
Synthesis 2008(19): 3108-3120  
DOI: 10.1055/s-2008-1067266
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Carbohydrate-Based Spiro-1,3-oxazolidine-2-thiones: Stereoselective Approaches Using Aziridines and Epoxides

Sébastien Tardya, Joana Lobo Vicentea, Arnaud Tatibouët*a, Gilles Dujardinb, Patrick Rollina
a ICOA UMR 6005 CNRS, Université d’Orléans, 45067 Orléans, France
e-Mail: arnaud.tatibouet@univ-orleans.fr;
b UCO2M UMR 6011 CNRS, Université du Maine, 72085 Le Mans, France
Further Information

Publication History

Received 30 April 2008
Publication Date:
05 September 2008 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

d-glucose and d-fructose have been used as starting materials to prepare spiro-1,3-oxazolidine-2-thiones anchored on the third position of both carbohydrates. Following different ap­proaches and depending on the carbohydrate template explored, stereoselective reactions have been developed via the formation of epoxides or aziridines.

Key words

azide - epoxide - spiro-compounds - chirality

    References

  • 1a Hultin PG. Earle MA. Sudarshan M. Tetrahedron  1997,  53:  14823 
    Search in Google Scholar
  • 1b Pellissier H. Tetrahedron  2007,  63:  3235 
    Search in Google Scholar
  • 1c Kunz H. Rück K. Angew. Chem., Int. Ed. Engl.  1993,  32:  336 
    Search in Google Scholar
  • 1d Dieguez M. Pamies O. Ruiz A. Diaz Y. Castillon S. Claver C. Coord. Chem. Rev.  2004,  248:  2165 
    Search in Google Scholar
  • 1e Boysen MMK. Chem. Eur. J.  2007,  13:  8648 
    Search in Google Scholar
  • For selected recent publications, see:
  • 2a Kim HJ. Kim Y. Choi ET. Lee MH. No ES. Park YS. Tetrahedron  2006,  62:  6303 
    Search in Google Scholar
  • 2b Kim HJ. Shin EK. Chang JY. Kim Y. Park YS. Tetrahedron Lett.  2005,  46:  4115 
    Search in Google Scholar
  • 2c Zimmer R. Orschel B. Scherer S. Reissig HU. Synthesis  2002,  1553 
  • 3a Huang H. Chen H. Hu X. Baiand C. Zheng Z. Tetrahedron: Asymmetry  2003,  14:  297 
    Search in Google Scholar
  • 3b Burke C. Shi Y. Angew. Chem. Int. Ed.  2006,  45:  4475 
    Search in Google Scholar
  • 3c Kang J. Jho Lim G. Kyoon Yoon S. Yoo Kim M. J. Org. Chem.  1995,  60:  564 
    Search in Google Scholar
  • 3d Bach T. Höfer F. J. Org. Chem.  2001,  66:  3427 
    Search in Google Scholar
  • 3e Frohn M. Shi Y. Synthesis  2000,  1979 
  • 4a Guz NR. Phillips AJ. Org. Lett.  2002,  4:  2253 
    Search in Google Scholar
  • 4b Zhang W. Carter RG. Yokochi AFT. J. Org. Chem.  2004,  69:  2569 
    Search in Google Scholar
  • 4c Jalce G. Seck M. Franck X. Hocquemiller R. Figadère B. J. Org. Chem.  2004,  69:  3240 
    Search in Google Scholar
  • 4d Chakraborty TK. Jayaprakash S. Laxman P. Tetrahedron  2001,  57:  9461 
    Search in Google Scholar
  • 4e Ortiz AK. Quintero L. Hernandez H. Maldonado S. Mendoza G. Bernes S. Tetrahedron Lett.  2003,  44:  1129 
    Search in Google Scholar
  • 4f Kinoshita H. Osamura T. Mizuno K. Kinoshita S. Iwamura T. Takahashi N. Iwamura T. Watanabe S.-I. Kataoka T. Muraoka O. Tanabe G. Tetrahedron Lett.  2005,  46:  7155 
    Search in Google Scholar
  • 4g Mendoza G. Hernandez H. Quintero L. Sosa-Rivadeneyra M. Bernes S. Sansinenea E. Ortiz A. Tetrahedron Lett.  2005,  46:  7867 
    Search in Google Scholar
  • 4h Kinoshita H. Osamura T. Mizuno K. Kinoshita S. Iwamura T. Watanabe S.-I. Kataoka T. Muraoka O. Tanabe G. Chem. Eur. J.  2006,  12:  3896 
    Search in Google Scholar
  • 4i Turconi J. Lebeau L. Paris J.-M. Mioskowski C. Tetrahedron Lett.  2006,  47:  121 
    Search in Google Scholar
  • 5a Crimmins MT. King BW. Tabet EA. Chaudhary K. J. Org. Chem.  2001,  66:  894 
    Search in Google Scholar
  • 5b Crimmins MT. McDougall PJ. Org. Lett.  2003,  5:  591 
    Search in Google Scholar
  • 5c Crimmins MT. Katz JD. Washburn DG. Allwein SP. McAtee LF. J. Am. Chem. Soc.  2002,  124:  5661 
    Search in Google Scholar
  • For examples, see:
  • 6a Saito Y. Zevaco TA. Agrofoglio LA. Tetrahedron  2002,  58:  9593 
    Search in Google Scholar
  • 6b Mio S. Kumagawa Y. Sugai S. Tetrahedron  1991,  47:  2133 
    Search in Google Scholar
  • 6c Guo J. Frost JW. J. Am. Chem. Soc.  2002,  124:  528 
    Search in Google Scholar
  • 7a Soler T. Bachki A. Falvello LR. Foubelo F. Yus M. Tetrahedron: Asymmetry  1998,  9:  3939 
    Search in Google Scholar
  • 7b Soler T. Bachki A. Falvello LR. Foubelo F. Yus M. Tetrahedron: Asymmetry  2000,  11:  493 
    Search in Google Scholar
  • 8 Maryanoff BE. Reitz AB. Nortey SO. Tetrahedron  1988,  44:  3093 
    CrossrefSearch in Google Scholar
  • 9a Lankin DC. Nugent ST. Rao SN. Carbohydr. Res.  1993,  244:  49 
    Search in Google Scholar
  • 9b Morin C. Ogier L. Tetrahedron: Asymmetry  2000,  11:  629 
    Search in Google Scholar
  • 10 Sahabuddin Sk. Ghosh R. Achari B. Mandal SB. Org. Biomol. Chem.  2006,  4:  551 
    CrossrefPubMedSearch in Google Scholar
  • 11a Garcia-Moreno MI. Diaz-Perez P. Benito JM. Ortiz-Mellet C. Defaye J. Garcia-Fernandez JM. Carbohydr. Res.  2002,  337:  2329 
    Search in Google Scholar
  • 11b Isoda T. Hayashi K. Tamai S. Kumagai T. Nagao Y. Chem. Pharm. Bull.  2006,  54:  1616 
    Search in Google Scholar
  • 11c Girniene J. Tardy S. Tatibouët A. Sackus A. Rollin P. Tetrahedron Lett.  2004,  45:  6443 
    Search in Google Scholar
  • 12a Alves RJ. Castillon S. Dessinges A. Herczegh P. Lopez JC. Lukacs G. Olesker A. Thang TT. J. Org. Chem.  1988,  53:  4616 
    Search in Google Scholar
  • 12b Kapferer P. Birault V. Poisson JF. Vasella A. Helv. Chim. Acta  2003,  86:  2210 
    Search in Google Scholar
  • 12c Bourgeois JM. Helv. Chim. Acta  1974,  57:  2553 
    Search in Google Scholar
  • 12d Bourgeois JM. Helv. Chim. Acta  1975,  58:  363 
    Search in Google Scholar
  • 12e Bourgeois JM. Helv. Chim. Acta  1976,  59:  2114 
    Search in Google Scholar
  • 13a Kapferer P. Birault V. Poisson J.-F. Vasella A. Helv. Chim. Acta  2003,  86:  2210 
    Search in Google Scholar
  • 13b Ahmadian M. Khare NK. Riordan JM. Klon AE. Borhani DW. Tetrahedron  2001,  57:  9899 
    Search in Google Scholar
  • 14a Fukuyama T. Jow CK. Cheung M. Tetrahedron Lett.  1995,  36:  6373 
    Search in Google Scholar
  • 14b Maligres PE. See MM. Askin D. Reider PJ. Tetrahedron Lett.  1997,  38:  5253 
    Search in Google Scholar
  • 14c Kroutil J. Karban J. Budesinsky M. Carbohydr. Res.  2003,  338:  2825 
    Search in Google Scholar