Skip to main content
SpringerLink
Log in

1,3-Dipolar Cycloadditions of Sugar-Derived Nitrones and their Utilization in Synthesis

  • Chapter
  • First Online:
Heterocycles from Carbohydrate Precursors

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 7))

Abstract

This review is devoted to the stereoselectivity of intermolecular (intramolecular cycloadditions are not included) 1,3-dipolar cycloadditions of sugar-derived nitrones. Stereoselective cycloaddition (transformation of isoxazolidine followed by reduction of the N–O bond to produce both an amino and a hydroxy function) allows the synthesis of tailor-made products of possible biological interest such as polyhydroxylated pyrrolidines, pyrrolizidines, indolizidines, β-aminocarbonyl compounds, and disaccharides. Attention is focused on the preparation of isoxazolidinyl nucleosides and to the catalysis of the cycloaddition by Lewis acids. This review has concentrated on the new developments achieved from 1999 to February 2007.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Tufariello JJ (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry. Wiley-Interscience, New York, p 83

    Google Scholar 

  2. Torssell KBG (1988) Nitrile oxides, nitrones, and nitronates in organic synthesis; novel strategies in synthesis. VCH, New York

    Google Scholar 

  3. Grünanger P, Vita-Finzi P (1991) Isoxazoles, part 1. In: Taylor EC, Weissberger E (eds) The chemistry of heterocyclic compounds. Wiley, New York

    Google Scholar 

  4. Chiacchio U, Genovese P, Iannazzo D, Librando V, Merino P, Rescifina A, Romeo R, Procopio A, Romeo G (2004) Tetrahedron 60:441

    Article  CAS  Google Scholar 

  5. Dondoni A, Franco S, Junquera F, Merchán F, Merino P, Tejero T (1994) Synth Commun 24:2537

    CAS  Google Scholar 

  6. Fišera L, Al-Timari UAR, Ertl P (1992) In: Gulliano E (ed) Cycloadditions in carbohydrate chemistry, ACS Monograph. Am Chem Soc, Washington, p 158

    Google Scholar 

  7. Merino P (2004) In: Padwa A (ed) Sciences of synthesis, vol 1. Thieme, Stuttgart, p 511

    Google Scholar 

  8. Tyler PC, Winchester BG (1999) In Stütz AE (ed) Iminosugars as glycosidase inhibitors. Nojirimycin and beyond. Wiley-VCH, Weinheim, p 125

    Google Scholar 

  9. El Ashry ESH, Rashed N, Shobier AHS (2000) Pharmazie 55:331

    Google Scholar 

  10. Asano N (2003) Glycobiology 13:93R

    Article  CAS  Google Scholar 

  11. Frederickson M (1997) Tetrahedron 53:403

    Article  CAS  Google Scholar 

  12. Gothelf KV, Jørgensen KA (1988) Chem Rev 98:86

    Google Scholar 

  13. Osborn HMI, Gemmel N, Harwood LM (2002) J Chem Soc Perkin Trans I 22:2419

    Article  CAS  Google Scholar 

  14. Koumbis AE, Gallos JK (2003) Current Org Chem 7:585

    Article  CAS  Google Scholar 

  15. Fišera L, Ondruš V, Kubán J, Micúch P, Blanáriková I, Jäger V (2000) J Heterocyclic Chem 37:551

    Article  Google Scholar 

  16. Jones RCF, Martin JN (2002) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. In: Padwa A, Pearson WH (eds) The chemistry of heterocyclic compounds, vol 59. Wiley, New York, p 1

    Google Scholar 

  17. Pellissier H (2007) Tetrahedron 63:3235

    Article  CAS  Google Scholar 

  18. Kubán J, Blanáriková I, Fengler-Veith M, Jäger V, Fišera L (1998) Chem Papers 52:780

    Google Scholar 

  19. Kubán J, Blanáriková I, Fišera L, Jarošková L, Fengler-Veith M, Jäger V, Kozíšek J, Humpa O, Prónayová N, Langer V (1999) Tetrahedron 55:9501

    Article  Google Scholar 

  20. Kubán J, Kolarovic A, Fišera L, Jäger V, Humpa O, Prónayová N, Ertl P (2001) Synlett, p 1862

    Google Scholar 

  21. Kubán J, Kolarovic A, Fišera L, Jäger V, Humpa O, Prónayová N (2001) Synlett, p 1866

    Google Scholar 

  22. Dugovic B, Fišera L, Hametner C (2004) Synlett, p 1569

    Google Scholar 

  23. Dugovic B, Fišera L, Cyranski MK, Hametner C, Prónayová N, Obranec M (2005) Helv Chim Acta 88:1432

    Google Scholar 

  24. Dugovic B, Wiesenganger T, Fišera L, Hametner C, Prónayová N (2005) Heterocycles 65:591

    Google Scholar 

  25. Dugovic B, Fišera L, Hametner C, Prónayová N (2003) ARKIVOC xiv:162

    Google Scholar 

  26. Dugovic B, Fišera L, Cyranski MK, Hametner C, Prónayová N (2004) Monatsh Chem 135:685

    Google Scholar 

  27. Liu PS (1987) J Org Chem 52:4717

    Article  CAS  Google Scholar 

  28. Cardona F, Salanski P, Chmielewski M, Valenza S, Goti A, Brandi A (1998) Synlett, p 1444

    Google Scholar 

  29. Merino P, Franco S, Merchan FL, Romero P, Tejero T, Uriel S (2003) Tetrahedron Asymmetry 14:3731

    Article  CAS  Google Scholar 

  30. Argyropoulos NG, Sarli VC (2004) Tetrahedron Lett 45:4237

    Article  CAS  Google Scholar 

  31. Torres-Sánchez I, Borrachero P, Cabrera-Escribano F, Gómez-Guillén M, Angulo-Álvarez M, Diánez J, Estrada D, López-Castro A, Pérez-Garrido S (2005) Tetrahedron Asymmetry 16:3897

    Article  CAS  Google Scholar 

  32. Borrachero P, Cabrera-Escribano F, Gómez-Guillén M, Torres M (2004) Tetrahedron Lett 45:4835

    Article  CAS  Google Scholar 

  33. Schweizer F (2002) Angew Chem Int Ed 41:230

    Article  CAS  Google Scholar 

  34. Borrachero P, Cabrera-Escribano F, Diánez J, Estrada D, Gómez-Guillén M, López-Castro A, Pérez-Garrido S, Torres I (2002) Tetrahedron Asymmetry 13:2025

    Article  CAS  Google Scholar 

  35. Karanjule NS, Markad SD, Sharma T, Sabharwal SG, Puranik VG, Dhavale DD (2005) J Org Chem 70:1356

    Article  CAS  Google Scholar 

  36. Li X, Takahashi H, Ohtake H, Ikegami S (2004) Tetrahedron Lett 45:4123

    Article  CAS  Google Scholar 

  37. Borrachero P, Cabrera F, Diánez J, Estrada D, Gómez-Guillén M, López-Castro A, Moreno J, de Paz JL, Pérez-Garrido S (1999) Tetrahedron Asymmetry 10:77

    Article  CAS  Google Scholar 

  38. Silva AMG, Tomé AC, Neves MGPM, Silva AMS, Cavaleiro JAS, Perrone D, Dondoni A (2002) Tetrahedron Lett 43:603

    Article  CAS  Google Scholar 

  39. Merino P (2002) Curr Med Chem Anti-Infective Agents 1:389

    Article  CAS  Google Scholar 

  40. Vorbrüggen H, Krolikiewicz K. Bennua B (1981) Chem Ber 114:1234

    Google Scholar 

  41. Fischer R, Drucková A, Fišera L, Rybár A, Hametner C, Cyrañski MK (2002) Synlett, p 1113

    Google Scholar 

  42. Hýrošová E, Fišera L, Jame RMA, Prónayová N, Medvecký M, Koóš M (2007) Chem Heterocyclic Compounds, p 80

    Google Scholar 

  43. Vasella A (1977) Helv Chim Acta 60:426

    Article  CAS  Google Scholar 

  44. Mzengeza S, Whitney RA (1988) J Org Chem 53:4074

    Article  CAS  Google Scholar 

  45. Chiacchio U, Rescifina A, Corsaro A, Pistara V, Romeo G, Romeo R (2000) Tetrahedron Asymmetry 11:2045

    Article  CAS  Google Scholar 

  46. Vasella A, Voeffray R (1982) Helv Chim Acta 65:1134

    Article  CAS  Google Scholar 

  47. Vasella A, Voeffray R, Pless J, Huguenin R (1983) Helv Chim Acta 66:1241

    Article  CAS  Google Scholar 

  48. Kasahara K, Iida H, Kibayashi C (1989) J Org Chem 54:2225

    Article  CAS  Google Scholar 

  49. Machetti F, Cordero FM, De Sarlo F, Guarna A, Brandi A (1996) Tetrahedron Lett 37:4205

    Article  CAS  Google Scholar 

  50. Tamura O, Mita N, Kusaka N, Suzuki H, Sakamoto M (1997) Tetrahedron Lett 38:429

    Article  CAS  Google Scholar 

  51. Chiacchio U, Corsaro A, Gumina G, Rescifina A, Iannazzo D, Piperno A, Romeo G, Romeo R (1999) J Org Chem 64:9321

    Article  CAS  Google Scholar 

  52. Borthakur DR, Prajapati D, Sandhu JS (1988) Ind J Chem 27B:724

    CAS  Google Scholar 

  53. Fišera L, Al-Timari UAR, Ertl P, Prónayová N (1993) Monatsh Chem 124:1019

    Article  Google Scholar 

  54. Cicchi S, Marradi M, Corsi M, Faggi C, Goti A (2003) Eur J Org Chem 4152

    Google Scholar 

  55. Cicchi S, Corsi M, Marradi M, Goti A (2002) Tetrahedron Lett 43:2741

    Article  CAS  Google Scholar 

  56. Merino P, Revuelta J, Tejero T, Chiacchio U, Rescifina A, Piperno A, Romeo G (2002) Tetrahedron Asymmetry 13:167

    Article  CAS  Google Scholar 

  57. Tamura O, Kanoh A, Yamashita M, Ishibashi H (2004) Tetrahedron 60:9997

    Article  CAS  Google Scholar 

  58. Chiacchio U, Corsaro A, Gumina G, Rescifina A, Iannazzo D, Piperno A, Romeo G, Romeo R (1999) J Org Chem 64:9321

    Article  CAS  Google Scholar 

  59. Chiacchio U, Corsaro A, Iannazzo D, Piperno A, Pistara V, Rescifina A, Romeo R, Sindona G, Romeo G (2003) Tetrahedron Asymmetry 14:2717

    Article  CAS  Google Scholar 

  60. Challand R, Young R (1998) Antiviral chemotherapy. Oxford University Press, Oxford

    Google Scholar 

  61. Chiacchio U, Corsaro A, Iannazzo D, Piperno A, Pistara V, Rescifina A, Romeo R, Valveri V, Mastino A, Romeo G (2003) J Med Chem 46:3696

    Article  CAS  Google Scholar 

  62. Merino P, Tejero T, Unzurrunzaga FJ, Franco S, Chiacchio U, Saita MG, Iannazzo D, Piperno A, Romeo G (2005) Tetrahedron Asymmetry 16:3865

    Article  CAS  Google Scholar 

  63. Yalowitz JA, Pankiewicz K, Patterson SE, Jayaram HN (2002) Cancer Lett 181:31

    Article  CAS  Google Scholar 

  64. Torrente S, Noya B, Branchadell V, Alonso R (2003) J Org Chem 68:4772

    Article  CAS  Google Scholar 

  65. Tamura O, Toyao A, Ishibashi H (2002) Synlett, p 1344

    Google Scholar 

  66. Argyropoulos NG, Panagiotidis T, Coutouli-Argyropoulos E, Raptopoulou C (2007) Tetrahedron 63:321

    Article  CAS  Google Scholar 

  67. Chevrier C, Le Nouen D, Neuburger M, Defoin A, Tarnus C (2004) Tetrahedron Lett 45:5363

    Article  CAS  Google Scholar 

  68. Cardona F, Faggi E, Liguori F, Cacciarini M, Goti A (2003) Tetrahedron Lett 44:2315

    Article  CAS  Google Scholar 

  69. Carmona T, Whigtman RH, Robina I, Vogel P (2003) Helv Chim Acta 86:3066

    Article  CAS  Google Scholar 

  70. Peer A, Vasella A (1999) Helv Chim Acta 82:1044

    Article  CAS  Google Scholar 

  71. Liauturd V, Christina AE, Desvergnes V, Martin OR (2006) 71:7337

    Google Scholar 

  72. Duff FJ, Vivien V, Wightman RH (2000) Chem Commun, p 2127

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237, Bratislava, Slovak Republic

    L. Fišera

Authors
  1. L. Fišera
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. Fišera .

Editor information

El Sayed H. El Ashry

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Fišera, L. (2007). 1,3-Dipolar Cycloadditions of Sugar-Derived Nitrones and their Utilization in Synthesis. In: El Ashry, E.S.H. (eds) Heterocycles from Carbohydrate Precursors. Topics in Heterocyclic Chemistry, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_076

Download citation

Publish with us

Policies and ethics

Search

Navigation