Mild and stereoconvergent palladium-catalyzed carbonyl alkenation reaction of α,β-unsaturated aldehydes

Synthesis

Volumn , Issue 1, 1998, Pages 83-88

  Braun, Manfred ^a   Mroß, Stefan ^a   Schwarz, Ido ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Aldol addition; Dienes; Elimination; Palladium catalysis

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031984422     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1995     Document Type: Article

References (29)

1. Cf. Heck, R. F. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon: Oxford 1991; p 833.
2. Tsuji, J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 19, 2075.
3. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 20, 2301.
4. Mandai, T.; Gotoh, J.; Otera, J.; Kawada, M. Chem. Lett. 1980, 313.
5. Åkermark, B.; Nyström, J. E.; Rein, T.; Bäckvall, J. E. Tetrahedron Lett. 1984, 25, 5719.
6. Takahashi, T.; Nakagawa, N.; Minoshima, T.; Yamada, H.; Tsuji, J. Tetrahedron Lett. 1990, 31, 4333.
7. Mandai, T.; Matsumoto, T.; Nakao, X.; Teramoto, H.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1992, 33, 2549.
8. Kumobayashi, H.; Mitsuhashi, S.; Akutagawa, S.; Ohtsuka, T. Chem. Lett. 1986, 157.
9. Suzuki, M.; Oda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623.
10. Trost, B. M.; Fortunak, J. M. J. Am. Chem. Soc. 1980, 102, 2841;
11. Tetrahedron Lett. 1981, 22, 3459.
12. Rathke, M. W.; Sullivan, D. F. J. Am. Chem. Soc. 1973, 95, 3050.
13. Heathcock, C. H. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon: Oxford 1991, p 181.
14. Kelly, S. E. In Comprehensive Organic Synthesis. Vol. 1; Trost, B. M., Ed.; Pergamon: Oxford 1991, p 729.
15. Cossentini, M.; Deschamps, B.; Anh, N. T.; Seyden-Penne, J. Tetrahedron 1977, 33, 409;
16. Deschamps, B.; Seyden-Penne, J. Tetrahedron 1977, 33, 413.
17. DiRenzo, G. M.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225.
18. Andersson, P. G.; Schab, S. Organometallics 1995, 14, 1.
19. Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723.
20. Devant, R.; Mahler, U.; Braun, M., Chem. Ber. 1988, 121, 397.
21. Heathcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Tetrahedron 1981, 23, 4087.
22. Katz, J. J.; Dubois, J. E.; Lion, C. Bull. Soc. Chim. Fr. 1977, 683.
23. Klages, A. Chem. Ber. 1902, 55, 2245.
24. Idoux, J. P.; Ghane, H., J. Chem. Eng. Data. 1979, 24, 157.
25. Hartzell, S. L.; Sullivan, D. F.; Rathke, M. W., Tetrahedron Lett. 1974, 15, 1403.
26. Kanemoto, N.; Sato, Y.; Inoue, S. J. Organomet. Chem. 1988, 348, 25.
27. Rosen, B. I.; Weber, W. P. J. Org. Chem. 1977, 42, 47.
28. Profft, E.; Linke, H. W. Chem. Ber. 1960, 93, 2591.
29. Descotes, G.; Robbe, P. Bull. Soc. Chim. Fr. 1969, 1349.