Anionic domino process for the one-pot, diastereoselective synthesis of dihydropyranols from β-nitroalcohols

Synlett

Volumn , Issue 14, 2004, Pages 2618-2620

  Ballini, Roberto ^a   Barboni, Luciano ^a   Fiorini, Dennis ^a   Palmieri, Alessandro ^a  

^a Dipto di Sci Chim dell'Universita   (Italy)

Author keywords

Anionic domino process; Diastereoselectivity; Dihydropyranols; Michael reaction; Nitroalkanols

Indexed keywords

3 HEXENE 2,5 DIONE; ACETAL DERIVATIVE; ACETONITRILE; ALCOHOL DERIVATIVE; ALLYL ALCOHOL; ANION; BETA NITROALCOHOL; DIHYDROPYRANOL DERIVATIVE; KETONE DERIVATIVE; NITRO DERIVATIVE; NITROALKANE; NITROUS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CYCLIZATION; DIASTEREOISOMER; MICHAEL ADDITION; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 9644302417     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834820     Document Type: Article

References (36)

1. See for example: (a) Polyether Antibiotics; Westley J. W., Marcel Dekker: New York, 1982.
2. (b) Barlett, P. A. In Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: New York, 1984.
3. Korte, F.; Claussen, U.; Göhring, K. Tetrahedron 1962, 18, 1257.
4. (a) Paquette, L.; Lanter, J. C.; Johnston, J. N. J. Org. Chem. 1997, 63, 1702.
5. (b) McErlean, C. S. P.; Fletcher, M. T.; Wood, B. J.; De Voss, J. J.; Kitching, W. Org. Lett. 2002, 4, 2775.
6. Reggelin, M.; Gerlach, M.; Vogt, M. Eur. J. Org. Chem. 1999, 1011.
7. (a) Duperrier, A.; Moreau, M.; Dreux, J.; Bouchu, M.-N. Bull. Soc. Chim. Fr. 1975, 2307.
8. (b) Duperrier, A.; Dreux, J. C. R. Acad. Sci. Ser. C 1969, 34.
9. Hall, N. Science 1994, 266, 32.
10. (a) Robinson, R. J. Chem. Soc. 1917, 111, 7.
11. (b) Schopf, C. Angew. Chem. 1937, 50, 779.
12. Posner, G. H. Chem. Rev. 1986, 86, 831.
13. Tietze, L. F. Chem. Rev. 1996, 96, 115.
14. Rodriguez, J. Synlett 1999, 505.
15. (a) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
16. (b) Rosini, G.; Ballini, R. Synthesis 1988, 833.
17. (c) Ballini, R. Studies in Natural Products Chemistry, Vol. 19; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1997, 117.
18. (d) Ballini, R. Synlett 1999, 1009.
19. (e) Ono, N. The Nitro Group in Organic Synthesis; John Wiley: New York, 2001.
20. (f) Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017.
21. See for example: (a) Ballini, R.; Rinaldi, A. Tetrahedron Lett. 1994, 35, 9247.
22. (b) Ballini, R.; Bosica, G. Tetrahedron 1995, 51, 4213.
23. (c) Ballini, R.; Bosica, G.; Fiorini, D.; Gil, M. V.; Petrini, M. Org. Lett. 2001, 3, 1265.
24. (d) Ballini, R.; Fiorini, D.; Gil, M. V.; Palmieri, A. Tetrahedron Lett. 2003, 44, 9033.
25. (a) Ballini, R.; Barboni, L.; Pintucci, L. Synlett 1997, 1389.
26. (b) Ballini, R.; Bosica, G.; Gigli, F. Tetrahedron 1998, 54, 7573.
27. (c) Ballini, R.; Barboni, L.; Bosica, G.; Filippone, P.; Peretti, S. Tetrahedron 2000, 56, 4095.
28. (d) Ballini, R.; Barboni, L.; Bosica, G.; Fiorini, D.; Gil, M. V.; Petrini, M. Tetrahedron 2001, 57, 6079.
29. (e) Ballini, R.; Fiorini, D.; Gil, M. V.; Palmieri, A. Tetrahedron Lett. 2003, 44, 9033.
30. (f) Ballini, R.; Fiorini, D.; Palmieri, A. Synlett 2003, 1704.
31. (g) Ballini, R.; Barboni, L.; Giarlo, G. J. Org. Chem. 2003, 68, 91.
32. β-Nitroalkanols 1 can be easily obtained by the nitroaldol (Henry) reaction of nitromethane with the appropriate aldehydes under several conditions. See for example: (a) Ballini, R.; Bosica, G.; Forconi, P. Tetrahedron 1996, 52, 1677.
33. (b) Ballini, R.; Bosica, G. J. Org. Chem. 1997, 62, 425.
34. (c) Ballini, R.; Bosica, G.; Livi, D.; Palmieri, A.; Maggi, R.; Sartori, G. Tetrahedron Lett. 2003, 44, 2271.
35. (d) Ballini, R.; Fiorini, D.; Gil, M. V.; Palmieri, A. Tetrahedron 2004, 60, 2799.
36. 3: C, 74.11; H, 7.39. Found: C, 74.32; H, 7.19.