First nickel-catalyzed 1,4-conjugate additions to α,β-unsaturated systems using triorganoindium compounds

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 10074-10076

  Férez, Ignacio ^a   Sestelo, José Férez ^a   Maestro, Miguel A ^b   Mourino, Antonio ^b   Sarandeses, Luis A ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDIUM; NICKEL;

ARTICLE; CATALYSIS; CONJUGATION;

EID: 0032567411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981830m     Document Type: Article

References (43)

1. (1)(a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, U.K., 1992.
2. (b) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1992; Vol. 4, p 169.
3. (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J.-L. J. Org. Chem. 1985,50,5761.
4. (b) Eshelby, J. J.; Crowley, P. J.; Parsons, P. J. Synlett 1993, 279.
5. Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053.
6. Westermann, J.; Nickisch, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1368.
7. (e) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron Lett. 1994, 35, 6075.
8. (f) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995,317.
9. (g) Westermann, J.; Imbery, U.; Nguyen, A. T.; Nickisch, K. Eur. J. Inorg. Chem. 1998, 295.
10. (a) Dupuy, C.; Petrier, C.; Sarandeses, L. A.; Luche, J.-L. Synth. Commun. 1991,21,643.
11. (b) Sarandeses, L. A.; Mourino, A. Luche, J-L. J. Chem. Soc., Chem. Commun. 1992, 798.
12. Pérez-Sestelo, J.; Mascarenas, J. L.; Castedo, L.; Mourino, A. J. Org. Chem. 1993, 58, 118.
13. For a review of the applications of indium in organic synthesis, see: Cintas, P. Synlett 1995, 1087.
14. (a) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988,53,1831.
15. (b) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538.
16. Araki, S.; Imai, A.; Shimizu, K.; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841.
17. (a) Li, C.-J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
18. (b) Kirn, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
19. Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228.
20. Maguire, R. J.; Mulzer, J.; Bats, J. W. J. Org. Chem. 1996, 61, 6936.
21. (e) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
22. (f) Yi, X.-H.; Meng, Y.; Li, C.-J. Chem. Commun. 1998, 449.
23. (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253.
24. (b) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453.
25. Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191.
26. Noraura, R.; Miyazaki, S.-I.; Matsuda, H. J. Am. Chem. Soc. 1992, 114, 2378.
27. Araki, S.; Shimizu, T.; Jin, S.-J.; Butsugan, Y. J. Chem. Soc., Chem. Commun. 1991, 824.
28. (a) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 709, 2393.
29. (b) Dayrit, F. M.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4466.
30. Negishi, E.-L; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596.
31. Krysan, D. J.; Mackenzie, P. B. J. Org. Chem. 1990,55, 4229.
32. Lipschutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283 and references therein.
33. (a) Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172.
34. (b) Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992,114, 5160.
35. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996,118,2099.
36. 10b
37. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978,43, 2923.
38. Brown, H. C. Organic Synthesis via Boranes; Wiley: New York, 1975; p 191.
39. Posner, G. H.; Whitten, C. E.; Sterling, J. J. J. Am. Chem. Soc. 1973, 95, 7788.
40. Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041.
41. Gendreau, Y.; Normant, J. F. Bull. Soc. Chim. Fr. 1979, 305.
42. Bertz, S. H.; Dabbagh, G. Tetrahedron 1989, 45, 425.
43. Boldrini, G. P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani Ronchi, A. J. Organomet. Chem. 1986, 301, C62.