Nickel-catalysed 1,4-addition of aryl groups to enones using aryldialkylaluminum compounds

European Journal of Inorganic Chemistry

Volumn , Issue 2, 1998, Pages 295-298

  Westermann, Jürgen ^a   Imbery, Ute ^a   Nguyen, Anh Thu ^a   Nickisch, Klaus ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

Conjugate addition; Enones; Steroids

Indexed keywords

ADDITION REACTIONS; KETONES; NICKEL;

ARYL GROUP; ARYL KETONES; CATALYTIC REACTIONS; CONJUGATE ADDITION; ENONE; NI(ACAC)2; STEROID; TRANSMETALLATION; ]+ CATALYST;

CATALYSIS;

EID: 0142259030     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0682(199802)1998:2<295::AID-EJIC295>3.0.CO;2-9     Document Type: Article

References (30)

1. P. Perlmutter in Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1992.
2. B. H. Lipshutz, Synthesis 1987, 325-341.
3. [3a] J. Westermann, K. Nickisch, Angew. Chem. 1993, 105, 1429; Angew. Chem. Int. Ed. Engl. 1993, 32, 1368.
4. [3a] J. Westermann, K. Nickisch, Angew. Chem. 1993, 105, 1429; Angew. Chem. Int. Ed. Engl. 1993, 32, 1368.
5. [3b] J. Westermann, S. Flemming, J. Kabbara, K. Nickisch, H. Neh, Synthesis 1995, 317-320.
6. [4a] K. Maruoka, H. Yamamoto, Tetrahedron 1988, 44, 5001.
7. [4b] I. Fleming, R. C. Moses, M. Tercel, J. Ziv. J Chem. Soc., Perkin Trans. 1 1991, 617.
8. [4c] A. Pecunioso, R. Menicagli, J. Org. Chem. 1988, 55, 45-49.
9. [4d] K. Rück, H. Kunz. Synlett 1992, 343.
10. [4e] E. C. Ashby, S A Noding, J. Org. Chem. 1979, 44, 4792-4797.
11. [5a] N. A. Bumagin, A. B. Ponomaryov, I. P. Beletskaya, Tetrahedron Lett. 1985, 26, 4819-4822.
12. [5b] A. Alberola et al., Synthesis 1984, 238-240.
13. [5c] K. H. Ahn, J. S. Kim, C. S. Jin, D. H. Kang, D. S. Han, Y. S. Shin, D. H. Kim, Synlett 1992, 306.
14. [5d] K. H. Kim et al., J. Heterocyd. Chem. 1993, 90, 825-827.
15. [6a] C. Petrier, J. C. de Souza Barbosa, C. Dupuy, J.-P. Luche, J. Org. Chem. 1985, 50, 5761-5765.
16. [6b] J. L. Luche, C. Petrier, J.-P. Lansard, A. E. Greene, J. Org. Chem. 1983, 48, 3837-3839.
17. S. Flemming, J. Kabbara, K. Nickisch, H. Nch, J. Westermann, Tetrahedron Lett. 1994, 35, 6075-6078.
18. [8a] J. A. Jeffery, A. Meisters, T. Mole, J Organomet. Chem. 1974, 74, 365.
19. [8b] E. C. Ashby, G. Heinsohn, J. Org. Chem. 1974, 39, 3297-3299.
20. [8c] J. Schwartz, D. B. Carr, R. T. Hansen, F. M. Dayrit, J. Org. Chem. 1980, 45, 3053-3061.
21. B. H. Lippshutz, D. A. Parker, J. A. Kozlowski, S. L. Nguyen, Tetrahedron Lett. 1984, 25, 5959.
22. [6a], see also: W. Tückmantel, K. Oshima, H.Nozaki, Chem. Ber. 1986, 119, 1581.
23. T. T. Takahashi, J. Y. Satoh, Bull. Chem. Soc. Jpn. 1976, 49, 1089-1072.
24. [12a] B. L. Shapiro, M. D. Johnston, M. J. Shapiro, Org. Magn. Reson. 1973, 5, 21-27.
25. [12b] M. Suzuki, T. Suzuki, T. Kawagashi, R. Noyori, Tetrahedron Lett. 1980, 21, 1247.
26. [12c] C. Pichat, Bull. Soc. Chim. Fr. 1949, 177, 183-184.
27. [12d] D. Pottin, J. Maddaluno, F. Dumas, Synth. Commun. 1990, 20, 2805-2813.
28. [12e] H. O. House, J. M. Wilkins, J. Org. Chem. 1978, 43, 2443-2454; G. Cahiez, M. Alami, Tetrahedron Lett. 1989, 27, 3541-3544.
29. [12e] H. O. House, J. M. Wilkins, J. Org. Chem. 1978, 43, 2443-2454; G. Cahiez, M. Alami, Tetrahedron Lett. 1989, 27, 3541-3544.
30. [12f] J. Westermann, H. Neh, K. Nickisch, Chem. Ber. 1996, 129, 963-966.