1,3-dipolar cycloaddition of D-xylose derived nitrone with methyl acrylate. Synthesis of chiral pyrrolidinones and pyrrolidines

Heterocycles

Volumn 84, Issue 1, 2011, Pages 683-696

  Podolan, Gabriel ^a   Fišera, Lubor ^a   Kožíšek, Jozef ^a   Fronc, Marek ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84855952222     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)44     Document Type: Article

References (35)

1. H. M. I. Osborn, N. Gemmel, and L. M. Harwood, J. Chem. Soc., Perkin Trans 1, 2002, 2419.
2. M. Frederickson, Tetrahedron 1997, 53, 403
3. K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 1998, 98, 863
4. P. Merino, S. Franco, F. L. Merchan, P. Romero, T. Tejero, and T. S. Uriel, Tetrahedron: Asymmetry, 2003, 14, 3731
5. A. E. Koumbis and J. K. Gallos, Curr. Org. Chem., 2003, 7, 585
6. H. Pellissier, Tetrahedron, 2007, 63, 3235.
7. L. Fišera, 1,3-Dipolar Cycloadditions of Sugar Derived Nitrones and their Utilization in the Synthesis. In: Heterocycles from Carbohydrate Precursors, ed. by E. S. H. El Ashry, Springer, Berlin, Heidelberg, 2007, pp. 287-324.
8. J. Kubán, I. Blanáriková, L. Fišera, L. Jarošková, M. Fengler-Veith, V. Jäger, J. Kožíšek, O. Humpa, N. Prónayová, and V. Langer, Tetrahedron, 1999, 55, 9501
9. J. Kubán, A. Kolarovic, L. Fišera, V. Jäger, O. Humpa, N. Prónayová, and P. Ertl, Synlett, 2001, 1862
10. J. Kubán, A. Kolarovic, L. Fišera, V. Jäger, O. Humpa, and N. Prónayová, Synlett, 2001, 1866.
11. J. W. Daly, T. F. Spande, and H. M. Garraffo, J. Nat. Prod., 2005, 68, 1556
12. C. Dong, F. Mo, and J. Wang, J. Org. Chem., 2008, 73, 1971.
13. P. C. Tyler and B. G. Winchester, "Iminosugars as Glycosidase Inhibitors. Nojirimycin and Beyond," ed. by A. E. Stütz, Wiley-VCH, Weinheim, 1999
14. N. Asano, R. J. Nash, R. J. Molyneux, and G. W. J. Fleet, Tetrahedron: Asymmetry, 2000, 11, 1645.
15. I. Delso, T. Tejero, A. Goti, and P. Merino, Tetrahedron, 2010, 66, 1220
16. A. Toyao, O. Tamura, H. Takagi, and H. Ishibashi, Synlett, 2003, 35
17. A. Toyao, O. Tamura, and H. Ishibashi, Synlett, 2002, 1344
18. A. T. Carmona, J. Fuentes, I. Robina, E. R. Garcia, R. Demange, P. Vogel, and A. L. Winters, J. Org. Chem., 2003, 68, 3874
19. I. Izquierdo, M. T. Plaza, R. Robles, and A. J. Mota, Eur. J. Org. Chem., 2000, 2071.
20. P. K. Upadhyay and P. Kumar, Synthesis, 2010, 3063.
21. I. Blanáriková-Hlobilová, Z. Kopanicá ková, L. Fišera, M. K. Cyranski, P. Salanski, J. Jurczak, and N. Prónayová, Tetrahedron, 2003, 59, 3333
22. B. Dugovic, T. Wiesenganger, L. Fišera, C. Hametner, and N. Prónayová, Heterocycles, 2005, 65, 591
23. B. Dugovic, L. Fišera, M. K. Cyranski, C. Hametner, N. Prónayová, and M. Obranec, Helv. Chim. Acta, 2005, 88, 1432.
24. R. Fischer, A. Drucková, L. Fišera, A. Rybár, C. Hametner, and M. K. Cyranski, Synlett, 2002, 1113.
25. R. Fischer, A. Drucková, L. Fišera, and C. Hametner, ARKIVOC, 2002, viii, 80
26. E. Hýrošová, L. Fišera, R. M. A. Jame, N. Prónayová, M. Medvecký, and M. Koóš, Chem. Heterocycl. Comp., 2007, 43, 10
27. E. Hýrošová, L. Fišera, J. Kožíšek, and M. Fronc, Synthesis, 2008, 1233
28. E. Hýrošová, M. Medvecký, L. Fišera, C. Hametner, H. Fröhlich, M. Marchetti, and G. Allmaier, Tetrahedron, 2008, 64, 3111.
29. P. Merino, E. M. Del Alamo, F. Santiago, F. L. Merchan, A. Simon, and T. Tejero, Tetrahedron: Asymmetry, 2000, 11, 1543
30. P. Merino, S. Franco, F. L. Merchan, and T. Tejero, J. Org. Chem., 2000, 65, 5575.
31. Crystallograhic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 829 834 and CCDC 829 835. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1E2, UK, (fax: +44 (0)1223 336033 or email: deposit@ccdc.cam.ac. uk ).
32. J. Rehák, L. Fišera, J. Kožíšek, L. Perašínová, B. Steiner, and M. Koóš, ARKIVOC, 2008, viii, 18
33. J. Rehák, L. Fišera, G. Podolan, J. Koží šek, and L. Perašínová, Synlett, 2008, 1260
34. J. Rehák, L. Fišera, J. Kožíšek, and L. Bellovicová, Tetrahedron, 2011, 67, 5762
35. G. Podolan, L. Klešcíková, L. Fišera, J. Kožíšek, and M. Fronc, Synlett, 2011, doi: 10.1055/s-0030-1260933.