Stereoconservative formation and reactivity of α-chalcogen- functionalized vinyllithium compounds from α-bromo-vinylic chalcogenides

Synlett

Volumn , Issue 5, 1997, Pages 595-596

  Braga, Antonio L ^a   Zeni, Gilson ^a   De Andrade, Leandro H ^a   Silveira, Claudio C ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000242470     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3227     Document Type: Article

References (33)

1. a) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett., 1994, 35, 7643.
2. b) Schlosser, M. (Ed.) Organometallics in Synthesis; John Wiley & Sons: Chichester, 1994.
3. c) Wakefield, B. J. In Organolithium Methods ; Academic Press: London, 1988, pp 21-52.
4. d) Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron, 1994, 50, 7987.
5. e) Najera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155.
6. f) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1994, 59, 1586.
7. a) Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett., 1991, 32, 6085.
8. b) Comasseto. J. V. J. Organomet. Chem. 1983, 253, 131.
9. c) Reich , H. J.; Willis Jr , W. W.; Clark, P. D. J. Org. Chem., 1981, 46, 2775.
10. d) Grobel, B. T.; Seebach, D. Chem. Ber. 1977, 110, 867.
11. e) Petragnani, N. Best Synthetic Methods - Tellurium in Organic Chemisty, Academic Press: London, 1994.
12. f) Denis, J. N.; Krief, A. Tetrahedron Lett. 1982, 23, 3411.
13. g) Fiandanese, V.; Marchese, G.; Mascolo, G.; Naso, F.; Ronzini, L. Tetrahedron Lett., 1988, 29, 3705.
14. Comasseto, J. V.; Menezes, P. H.; Stefani, H. A.; Zeni, G.; Braga, A. L. Tetrahedron 1996, 52, 9687.
15. a) Braga, A.L.; Reckziegel, A.; Silveira, C. C.; Comasseto, J. V. Synth. Commun. 1994, 24, 1165.
16. b) Coutrot, C.; Grisson, C.; Youssefi-Tabrizi, M. Synthesis 1987, 169.
17. c) Radchenko, S. I. Zh. Org. Chem. 1991, 27, 1597.
18. 26 S Te: C, 48.00; H, 5.76%; found C, 48.25; H, 5.61%.
19. Preparation of 1: 1a (E/Z = 100/0), 1b (100/0), 1e (75/25): according to ref. 3. 1c (100:0), 1d (100:0): according to ref. 4c.
20. a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis, 1976, 245.
21. b) Newmann, H.; Seebach, D. Chem. Ber. 1978, 11, 2785.
22. c) Shinokubo, H.; Miki, H.; Yokoo, T.; Oshima, K.; Utimoto, K. Tetrahedron 1995, 43, 11681.
23. Dabdoub, M. J.; Cassol, T. M.; Barbosa, S. L. Tetrahedron Lett. 1996, 57, 831.
24. Degl'Innocenti, A.; Ulivi, P.; Capperucci, A.; Mordini, A.; Reginato, G.; Ricci, A. Synlett, 1992, 499.
25. For (Te/Te) ketene acetals: Silveira, C. C.; Perin, G.; Braga, A. L. Tetrahedron Lett. 1995, 36, 7361.
26. Stang, P. J.; Roberts, K.; Lynch, L. E. J. Org. Chem. 1984, 49, 1653.
27. (Se/Se): Wautier, H.; Desauvage, S.; Hevesi, L. J. Chem. Soc., Chem. Commun. 1981, 738.
28. Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christel, H. J. Org. Chem. 1986, 51, 875.
29. Shin, W. S. S.; Lee. K.; Oh, D. Y. Tetrahedron Lett. 1992, 37, 5375.
30. (S/S) Kolb, M. Synthesis, 1990, 171.
31. Mikolajckyk, M.; Balczewski, P. Tetrahedron, 1992, 48, 8697.
32. a) Lemarie, L.; Valee, Y.; Worrell. M. Tetrahedron Lett. 1992, 33, 6131.
33. b) Harirchian B.; Magnus, P. D. J. Chem. Soc., Chem. Commun. 1977, 522.