ω-Halogeno polyenals: Preparation and application to a one-pot synthesis of polyenals from carbonyl compounds

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1997, Pages 1639-1645

  Soullez, David ^a   Plé, Gérard ^a   Duhamel, Lucette ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748648169     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a608187h     Document Type: Article

References (31)

1. (a) W. Fischetti, K. T. Mak, F. G. Stakem, J. I. Kim, A. L. Rheingold and R. F. Heck, J. Org. Chem., 1983, 48, 948;
2. (b) D. Diez-Martin, P. Grice, H. C. Kolb, S. V. Ley and A. Madin, Synlett, 1990, 326;
3. (c) Y. Le Gallic, PhD Thesis, University of Rouen, 1992;
4. (d) L. Duhamel, P. Duhamel and Y. Le Gallic, Tetrahedron Lett., 1993, 34, 319.
5. (a) T. V. Protopopova and A. P. Skoldinov, Khim. Nauka. Promst., 1958, 3, 536
6. (Chem. Abstr., 1960, 53, 4127c);
7. (b) Z. Arnold and J. Zemlicka, Collect. Czech. Chem. Commun., 1959, 34, 2378.
8. B. A. Patel, J. I. Kim, D. D. Bender, L. C. Kao and R. F. Heck, J. Org. Chem., 1981, 46, 1061;
9. A. I. Meyers, K. A. Babiak, A. L. Campbell, D. L. Comins, M. P. Fleming, R. Henning, M. Heuschmann, J. P. Hudspeth, J. M. Kane, P. J. Reider, D. M. Roland, K. Schimizu, T. Kyoshi and R. D. Walkup, J. Am. Chem. Soc., 1983, 105, 5015.
10. I. Marek and J. F. Normant, Synlett, 1993, 386.
11. L. Duhamel, P. Duhamel and J. P. Lecouvé, Tetrahedron, 1987, 43, (a) 4339; (b) 4349;
12. (c) L. Duhamel, G. Plé and Y. Ramondenc, Tetrahedron Lett., 1989, 30, 7377.
13. (d) Y. Ramondenc and G. Plé, Tetrahedron, 1993, 49, 10 855.
14. Preliminary note: D. Soullez, G. Plé, L. Duhamel and P. Duhamel, J. Chem. Soc., Chem. Commun., 1995, 563.
15. J. Becher, Synthesis, 1980, 589;
16. Org. Synth., 1979, 59, 79.
17. R. Grée, H. Tourbah and R. Carrié, Tetrahedron Lett., 1986, 27, 4983.
18. M. Matsumoto and K. Kuroda, Tetrahedron Lett., 1980, 21, 4021.
19. L. Duhamel and F. Tombret, J. Org. Chem., 1981, 46, 3741;
20. L. Duhamel, F. Tombret and Y. Mollier, J. Organomet. Chem., 1985, 280, 1.
21. B. Contreras, L. Duhamel and G. Plé, Synth. Commun., 1990, 20, 2983.
22. L. Duhamel, J. Guillemont, Y. Le Gallic, G. Plé, J. M. Poirier, Y. Ramondenc and P. Chabardes, Tetrahedron Lett., 1990, 31, 3129.
23. Reagents for trivinylogation: In one step: see refs. 5(c),(d), 12, and (a) K. Hemming and R. J. K. Taylor, J. Chem. Soc., Chem. Commun., 1993, 1409;
24. (b) D. Soullez, Y. Ramondenc, G. Plé and L. Duhamel, Nat. Prod. Lett., 1994, 4, 203;
25. (c) M. Bellassoued, E. Reboul and M. Salemkour, Synth. Commun., 1995, 25, 3097, 3108.
26. In two steps: see ref. 5(d), and (d) E. J. Corey and D. Enders, Tetrahedron Lett., 1976, 3;
27. (e) J. M. Williams and G. J. MacGarvey, Tetrahedron Lett., 1985, 26, 4891.
28. In three steps: see ref. 13(e) and (f) K. C. Nicolaou, T. K. Chakraborty, R. A. Daines and N. S. Simpkins, J. Chem. Soc., Chem. Commun., 1986, 413;
29. (g) M. Kinoshita, H. Takami, M. Taniguchi and T. Tamai, Bull. Chem. Soc. Jpn., 1987, 60, 2151.
30. Reagents for tetravinylogation: In two steps: see ref. 5(d) and S. D. Pychnovsky and R. C. Hoye, J. Am. Chem. Soc., 1994, 116, 1753.
31. Reagents for pentavinylogation: In three steps: C. S. Poss, S. D. Pychnovsky and S. L. Schreiber, J. Am. Chem. Soc., 1993, 115, 3360.