A Study of the influence of base, temperature and reaction time in nitroaldol reactions using (R)-(+)-glyceraldehyde acetonide: Diastereoselective synthesis of (4R, 5R)-dihydro-5-((R)-1,2-dihydroxyethyl)-4-nitrofuran-2(3H)-one

Letters in Organic Chemistry

Volumn 6, Issue 2, 2009, Pages 110-114

  Pennaforte, Érica V ^a   Costa, Jeronimo S ^b   Silva, Cristiane A ^a   Saraiva, Marcelo C ^c   Pereira, Vera L P ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b Centro Federal de Educação Tecnológica de Química CEFETQ   (Brazil)

^c PFIZER INC   (United States)

Author keywords

lactones; Henry reaction; Nitroalkanes; Nitronate ions; Tetrabutylammonium fluoride

Indexed keywords

EID: 69249200592     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809787582771     Document Type: Article

References (42)

1. Seebach, D.; Colvin, E. W.; Leher, F.; Weller, T. Chimia, 1979, 33,1.
2. Rosini, G.; Ballini, R. Synthesis, 1988, 833-847.
3. Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp. 321-340.
4. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: 2001, New York, Vol. 3, pp. 30-70.
5. Luzzio, F. A. Tetrahedron, 2001, 57, 91.
6. Shibata, N.; Katoh, T.; Terashima, S.; Tetrahedron Lett., 1997, 38, 619.
7. Koskinen, P. M; Koskinen, A. M. P. Synthesis, 1998, 1075.
8. El Blidi, L.; Crestia, D.; Gallienne, E.; Demuynck, C.; Bolte, J.; Lemaire, M. Tetrahedron Asymmetry, 2004, 15, 2951.
9. Hanessian, S.; Brassard, M. Tetrahedron, 2004, 60, 1017.
10. Solladié-Cavallo, A.; Khiar, N. Tetrahedron Lett., 1988, 29, 2189.
11. Solladié-Cavallo, A.; Khiar, N. J. Org. Chem., 1990, 55, 4750.
12. Bauer, T.; Jezewski, A.; Chapuis, C.; Jurczak, J. Tetrahedron Asymmetry, 1996, 7, 1385.
13. Kudyba, I.; Raczko, J.; Z.; Urbanczyk-Lipkowska, Z.; Jurczak, J.; Tetrahedron, 2004, 60, 4807.
14. Shibasaki, M.; Yoshikawa, N. Chem. Rev., 2002, 102, 2187.
15. (a) Du, D.; Lu, S.; Fang, T.; Xu, J. J. Org. Chem., 2005, 70, 3712 and references cited.
16. (b) Zhong, Y. Tian, P.; Lin, G. Tetrahedron Asymmetry, 2004, 15, 771 and references cited.
17. (c) For recent reviews on catalytic asymmetric Henry reactions see Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron Asymmetry, 2006, 17, 3315.
18. Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem., 2007, 16, 2561.
19. Sohtome, Y.; Takemura, N.; Iguchi, T.; Hashimoto, Y.; Nagasawa, K. Synlett, 2006,144 and references cited.
20. Hanessian, S.; Franco. J.; Larouche, B. Pure Appl. Chem., 1990,62, 1887.
21. Kozikowski, A.P.; Kitagawa, Y.; Springer, J.P. J. Chem. Soc. Chem. Commun., 1983, 1460.
22. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Eng., 1990, 29, 1169.
23. Hanessian, S.; Kloss, J. Tetrahedron Lett., 1985, 26, 1261.
24. Jäger, V.; Wehner, V.; Griesser, H.; Öhrlein, R.; Menzel, A. Synthesis, 1999, 9, 1691.
25. Jäger, V.; Öhrlein, R.; Wehner, V.; Poggendorf, P.; Steuer, B.; Raczko, J.; Griesser, H.; Kiess, F. M.; Menzel, A. Enantiomer, 1999, 4, 205.
26. Hanessian, S.; Devasthale, P. Tetrahedron Lett., 1996, 37, 987.
27. For examples of nitroaldol reactions using chiral non-racemic aldehydes and chiral catalysts see Corey, E. J.; Zhang, F. Y. Angew. Chem. Int. Ed. Engl., 1999, 38, 1931.
28. For example of nitroaldol reaction using both chiral non-racemic nitroalkane and aldehyde see Kiess, F. M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun., 1998,119.
29. (a) Cherest, M.; Felkin, H. Tetrahedron Lett., 1968, 2205.
30. (b) Anh, N. T.; Eisenstein, O. Tetrahedron Lett., 1976, 155.
31. (c) Bürgi, H. B., Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563.
32. (d) Anh, N.T. Top. Curr. Chem., 1980, 145.
33. (e) Mengel, A.; Reiser, O. Chem. Rev., 1999, 99, 1191.
34. Pinto, A. C.; Freitas, C. B. L.; Dias A.G.; Pereira, V. L. P.; Tinant, B.; Declercq, J.; Costa, P. R. R. Tetrahedron Asymmetry, 2002, 13, 1025.
35. Silva, P. C.; Costa, J. S.; Pereira, V.L.P. Synthetic Commun., 2001, 31, 595.
36. Costa, J. S.; Dias, A. G.; Anholeto, A. L.; atrocinio, V. L.; Costa, P. R. R. J. Org. Chem., 1997, 62, 4002.
37. Patrocinio, V. L.; Correia, C. R. D.; Costa, P. R. R. Synthesis, 1994, 474.
38. Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp, A. K. J. Am.Chem. Soc., 2005, 127, 5376 and references cited. For review, see: Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E.; Soloshonok, V. A. Eds.; John Wiley: Hoboken, 2005.
39. Mori, K.; Otsuka, T.; Oda, M., Tetrahedron, 1984, 40, 2929.
40. Mann, J.; Partlett, N. k.; Thomas, A. J. Chem. Res. (S), 1987, 369.
41. Öhrlein, R.; Schwab, W.; Ehrler, R.; Jäger, V. Synthesis, 1986, 535.
42. Ballini, R.; Petrini, M.; Rosini, G. Synthesis, 1986, 849.