Synthesis of chiral 2-furyl and 3-nitro-7-oxabicyclo[2.2.1]heptane derivatives from sugars

Tetrahedron Asymmetry

Volumn 20, Issue 17, 2009, Pages 1999-2006

  Araújo, Noelia ^a   Gil, María V ^a   Román, Emilio ^a   Serrano, José A ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIDEOXY 1 NITROALKENE DERIVATIVE; 2 GLYCO 4 METHYL 3 NITRO 7 OXABICYCLO[2.2.1]HEPTANE DERIVATIVE; 2 METHYLFURAN; 3 NITRO 7 OXABICYCLO[2.2.1]HEPTANE DERIVATIVE; 5,6 EXO EPOXY 2 GLYCO 3 NITRO 7 OXABICYCLO[2.2.1]HEPT 5 ENE DERIVATIVE; ALKENE DERIVATIVE; CARBOHYDRATE DERIVATIVE; FURAN DERIVATIVE; GALACTOSE; HEPTANE DERIVATIVE; MANNOSE; NITROALKENE DERIVATIVE; PENTA O ACETYL 1' C(4 METHYL 3 NITRO 7 OXABICYCLO[2.2.1]HEPT 5 EN 2 YL)PENTITOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 70349199033     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.07.026     Document Type: Article

References (38)

1. Hayashi Y. In: Kobayashi S., and Jorgensen K.A. (Eds). Cycloaddition Reactions in Organic Synthesis. Catalytic Asymmetric Diels-Alder Reactions (2001), Wiley-VCH, Weinheim 5
2. Evans D.A., and Barnes D.M. Tetrahedron Lett. 38 (1997) 57
3. Burke M.J., Allan M.M., Parvez M., and Keay B.A. Tetrahedron: Asymmetry 11 (2000) 2733 and references cited therein
4. Fraile J.M., García J.I., Gracia D., Mayoral J.A., and Pires E. J. Org. Chem. 61 (1996) 9479
5. Araújo N., Gil M.V., Román E., and Serrano J.A. Synthesis (2006) 2503
6. Araújo N., Cumbrera F.L., Gil M.V., Ortiz A.L., Román E., and Serrano J.A. Synlett (2008) 687
7. Basso A., Banfi L., Riva R., and Guanti G. J. Org. Chem. 70 (2005) 575
8. Bunnage M.E., Ganesh T., Masesane B.I., Orton D., and Steel P.G. Org. Lett. 5 (2003) 239
9. Ramza J., and Zamojski A. Tetrahedron 48 (1992) 6123
10. Maeba I., Iwata K., Usami F., and Furukawa H. J. Org. Chem. 48 (1983) 2998
11. Maeba I., Usami F., and Furukawa H. J. Org. Chem. 49 (1984) 1534
12. Ulgar V., López O., Maya I., Fernández-Bolaños J.G., and Bols M. Tetrahedron 59 (2003) 2801
13. Moreno-Vargas A.J., Jiménez-Barbero J., and Robina I. J. Org. Chem. 68 (2003) 4138
14. Sharma G.V.M., Reddy V.G., and Krishna P.R. Tetrahedron Lett. 40 (1999) 1783
15. Yadav J.S., Reddy B.V.S., Raman J.V., Niranjan N., Kumar S.K., and Kunwar A.C. Tetrahedron Lett. 43 (2002) 2095
16. Jarosz S., Mach M., Szewczyk K., Skóra S., and Ciunik Z. Eur. J. Org. Chem. (2001) 2947
17. Bartoli G., Fernández-Bolaños J.G., Di Antonio G., Foglia G., Giuli S., Gunnella R., Mancinelli M., Marcantoni E., and Paoletti M. J. Org. Chem. 72 (2007) 6029
18. Misra A.K., and Agnihotri G. Carbohydr. Res. 339 (2004) 1381
19. Sowden J.C., and Schaffer R. J. Am. Chem. Soc. 73 (1950) 4662
20. Sowden J.C., and Strobach D.R. J. Am. Chem. Soc. 82 (1960) 954
21. 2, they could be charged with 8 g of 1a, and with 2 g of 1b.
22. For a comparative discussion, Scheme 1 and Table 1 also reflect data from previously reported reactions between chiral nitroalkenes 1a or 1b with furan, and 1b with 2,5-dimethylfuran.
23. Franck R.W., Argade S., Subramaniam C.S., and Frechet D.M. Tetrahedron Lett. (1985) 3187
24. Román E., Hodgson J.D., Yokomori Y., Eliel E.L., Bueno M., and Serrano J.A. Carbohydr. Res. 180 (1988) 263
25. Fleming I. Frontier Orbitals and Chemical Reactions (1976), Wiley, London
26. Balthazor T.M., Gaede B., Korte D.E., and Shieh H.-S. J. Org. Chem. 49 (1984) 4547
27. Yuŕev, Y. K.; Zefirov, N. S.; Ivanova, R. A. Zh. Obshch. Khim. 1963, 33, 3512; Chem. Abstr. 1964, 60, 7971.
28. Eggelte T.A., de Koning H., and Huisman H.O. Heterocycles 4 (1976) 19
29. Ranganatham D., Rao C.B., Ranganatham S., Mehrotra A.K., and Iyengar R. J. Org. Chem. 45 (1980) 1185
30. Moore J.A., and Partain III E.M. J. Org. Chem. 48 (1983) 1105
31. Itoh K., Kitoh K., and Sera A. Heterocycles 51 (1999) 243
32. Itoh K., Kitoh K., and Kishimoto S. Can. J. Chem. 84 (2006) 392
33. Bossard P., and Eugster C.H. Adv. Heterocycl. Chem. 7 (1966) 377
34. Butin A.V., Stroganova T.A., Lodina I.V., and Krapivin G.D. Tetrahedron Lett. 42 (2001) 2031
35. Castagnino E., D́Auria M., De Mico A., D́Onofrio F., and Piancatelli G. J. Chem. Soc., Chem. Commun. (1987) 907
36. Baños M., Román E., and Serrano J.A. Tetrahedron: Asymmetry 14 (2003) 1187
37. Jackman L.M., and Sternhell S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry. 2nd ed. (1969), Pergamon, Oxford
38. Michael J.P., Maqutu T.L., and Howard A.S. J. Chem. Soc., Perkin Trans. 1 (1989) 2389