A broadened scope for the use of hydrazones as neutral nucleophiles in the presence of H-bonding organocatalysts

Synlett

Volumn , Issue 2, 2006, Pages 239-242

  Pettersen, Daniel ^a   Herrera, Raquel P ^a   Bernardi, Luca ^a   Fini, Franscesco ^a   Sgarzani, Valentina ^a   Fernandez, Rosario ^b   Lassaletta, José M ^c   Ricci, Alfredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF SEVILLE   (Spain)

^c INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

Addition reactions; Catalysis; Hydrazones; Ionic liquids; Nucleophiles

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; AZOMETHINE YLIDE; FORMALDEHYDE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; LEWIS ACID; THIOUREA DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DECOMPOSITION; HYDROGEN BOND; REACTION ANALYSIS; REACTION TIME;

EID: 32344453167     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922791     Document Type: Article

References (29)

1. (a) Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokoyama, T. J. Org. Chem. 1988, 53, 129.
2. (b) Kamitori, Y.; Hojo, M.; Masuda, R.; Yoshida, T.; Ohara, S.; Yamada, K.; Yoshikawa, N. J. Org. Chem. 1988, 53, 519.
3. (a) Brehme, R.; Nikolajewski, H. E. Tetrahedron 1969, 25, 1159.
4. (b) Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131.
5. (c) Brehme, R.; Reck, G.; Schulz, B.; Redeglia, R. Synthesis 2003, 1620.
6. Lassaletta, J. M.; Fernández, R. Synlett 2000, 1228.
7. Lassaletta, J. M.; Fernández, R.; Gasch, C.; V́azquez, J. Tetrahedron 1996, 52, 9143; and references therein.
8. (a) Fernández, R.; Martín-Zamora, E.; Pareja, C.; Lassaletta, J. M. J. Org. Chem. 2001, 66, 5201.
9. (b) Fernández, R.; Martín-Zamora, E.; Pareja, C.; Vázquez, J.; Díez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem. Int. Ed. 1998, 37, 3428.
10. Enders, D.; Vázquez, J.; Raabe, G. Eur. J. Org. Chem. 2000, 6, 893.
11. (a) Vázquez, J.; Prieto, A.; Fernández, R.; Enders, D.; Lassaletta, J. M. Chem. Commun. 2002, 498.
12. (b) Lassaletta, J. M.; Vázquez, J.; Prieto, A.; Fernández, R.; Raabe, G.; Enders, D. J. Org. Chem. 2003, 68, 2698.
13. Vázquez, J.; Cristea, E.; Díez, E.; Lassaletta, J. M.; Prieto, A.; Fernández, R. Tetrahedron 2005, 61, 4115.
14. (a) Lassaletta, J. M.; Fernández, R.; Martín-Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002.
15. (b) Díez, E.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M.; Martín-Zamora, E.; Vázquez, J. J. Org. Chem. 1997, 62, 5144.
16. (a) Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J.-M.; Vázquez, J. Tetrahedron Lett. 1993, 34, 141.
17. (b) Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M. Synthesis 1996, 48.
18. Dixon, D. J.; Tillman, A. L. Synlett 2005, 2635.
19. (a) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
20. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
21. (a) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
22. (b) Wittkopp, A.; Schreiner, P. R. Chem.-Eur. J. 2003, 9, 407.
23. (a) Dessole, G.; Herrera, R. P.; Ricci, A. Synlett 2004, 2374.
24. (b) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem. Int. Ed. 2005, 44, 6576.
25. Formation of adducts derived from attack by the azomethine carbon was not observed for any of the studied hydrazones 2b-f.
26. Lassaletta, J. M.; Fernández, R.; Martín-Zamora, E.; Pareja, C. Tetrahedron Lett. 1996, 37, 5787.
27. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Tetrahedron Lett. 2003, 44, 2217.
28. 2.
29. Fujim, K.; Node, M. Synlett 1991, 603.