Studies on the niobium pentachloride-mediated nucleophilic additions to an enantiopure cyclic N-acyliminium ion derived from (S)-malic acid

Journal of the Brazilian Chemical Society

Volumn 16, Issue 3 B, 2005, Pages 535-539

  Andrade, Carlos Kleber Z ^a   Rocha, Rafael O ^a   Russowsky, Dennis ^b   Godoy, Marla N ^b  

^a UNIVERSITY OF BRASILIA   (Brazil)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

Diastereoselectivity; N acyliminium ions; Niobium pentachloride; Nucleophilic additions

Indexed keywords

EID: 23744454184     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532005000400007     Document Type: Article

References (20)

1. Speckamp, W. N.; Moolenaar, M. J.; Tetrahedron 2000, 56, 3827.
2. See, for example: Pilli, R. A.; Dias, L. C.; Maldaner, A. O.; J. Org. Chem. 1995, 60, 717;
3. Dhimane, H.; Vanucci, C.; Lhommet, G.; Tetrahedron Lett. 1997, 38, 1415;
4. Bennet, D. J.; Blake, A. J.; Cooke, P. A.; Godfrey, C. R. A.; Pickering, P. L.; Simpkins, N. S.; Walker, M. D.; Wilson, C.; Tetrahedron 2004, 60, 4491;
5. Osante, I.; Lete, E.; Sotomayor, N.; Tetrahedron Lett. 2004, 45, 1253. See also ref. 3.
6. Pilli, R. A.; Russowsky, D.; J. Org. Chem. 1996, 61, 3187.
7. Andrade, C. K. Z.; Matos, R. A. F.; Synlett 2003, 1189.
8. 5 as Lewis acid, see: Andrade, C. K. Z.; Azevedo, N. R.; Oliveira, G. R.; Synthesis 2002, 928;
9. Andrade, C. K. Z.; Azevedo, N. R.; Tetrahedron Lett. 2001, 42, 6473;
10. Andrade, C. K. Z.; Oliveira, G. R.; Tetrahedron Lett. 2002, 43, 1935;
11. Andrade, C. K. Z.; Kalil, P. P.; Rocha, R. O.; Alves, L. M.; Panisset, C. M. A.; Lett. Org. Chem. 2004, 1, 109. See also ref. 4.
12. 5 applications in Organic Synthesis, see: Andrade, C. K. Z.; Curr. Org. Synth. 2004, 1, 333.
13. This work was presented at the X Brazilian Meeting on Organic Synthesis (BMOS): Andrade, C. K. Z.; Rocha, R. O.; Russowsky, D. August, 2003, São Pedro, SP, Brazil.
14. Koot, W. -J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401.
15. Russowsky, D.; Petersen, R. Z.; Godoi, M. N.; Pilli, R. A.; Tetrahedron Lett. 2000, 41, 9939.
16. Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406;
17. Koot, W. -J.; Van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Lonwrier, S.; Moolenaar, M. J.; Speckamp, W. N.; Tetrahedron Lett. 1991, 32, 401;
18. Lennartz, M.; Sadakane, M.; Steckhan, E.; Tetrahedron 1999, 55, 14407;
19. Klitzke, C. F.; Pilli, R. A.; Tetrahedron Lett. 2001, 42, 5605.
20. For an example, see: Ollero, L.; Mentink, G.; Rutjes, F. P. J. T; Speckamp, W. N.; Hiemstra, H.; Org. Lett. 1999, 1, 1331. See also ref. 4.