Stereospecific formation of chalcogenoenynes via palladium catalysed cross-coupling reaction of α-bromovinylic chalcogenides

Synthesis

Volumn , Issue 1, 1998, Pages 39-41

  Braga, Antonio L ^a   Zeni, Gilson ^a   De Andrade, Leandro H ^a   Silveira, Claudio C ^a   Stefani, Hélio A ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Cross coupling; Enynes; Vinylic bromide; Vinylic chalcogenide

Indexed keywords

ALKYNE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; GAS LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031974334     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2006     Document Type: Article

References (27)

1. Stutz, A. Angew. Chem. 1987, 99, 323;
2. Angew. Chem., Int. Ed. Engl. 1987, 26, 320.
3. Nussbaumer, P.; Leitner, L.; Mraz, K.; Stutz, A. J. Med. Chem. 1995, 38, 1831.
4. Alami, M.; Ferri, F.; Gaslain, Y. Tetrahedron Lett. 1996, 37, 57.
5. Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyake, T.; Oki, T.; Kawaguchi, H.; Van Duyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449.
6. Lee, M. D.; Dunne, T. S.; Chang, C.C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
7. Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
8. Yoshimatsu, M.; Hayashi, M.; Tanabe, G.; Muraoka, O. Tetrahedron Lett. 1996, 37, 4161.
9. Aksela, R.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1163 and references cited therein.
10. Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975.
11. Magnus, P.; Hirokazo, A.; Harling, J. J. Org. Chem. 1990, 55, 1709.
12. Nishikawa, T.; Shibuya, S.; Isobe, M. Synlett 1994, 482.
13. Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209 and references cited therein.
14. Eckhardt, M.; Bruckner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167.
15. Magriotis, P. A.; Doyle, T. J.; Kim, K. D. Tetrahedron Lett. 1990, 31, 2541.
16. Babudri, F.; Fiandanese, V.; Mazzone, L.; Naso, F. Tetrahedron Lett. 1994, 35, 8847.
17. Dabdoub, M. J.; Dabdoub, V.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 2261.
18. Marino, J. P.; Tucci, F.; Comasseto, J. V. Synlett 1993, 761.
19. Koreeda, M.; Yang, W. Synlett 1994, 201.
20. Comasseto, J. V.; Menezes, P. H.; Stefani, H. A.; Zeni, G.; Braga, A. L. Tetrahedron 1996, 52, 9687.
21. Braga, A. L.; Reckziegel, A.; Silveira, C. C.; Comasseto, J. V. Synth. Commun. 1994, 24, 1165.
22. Braga, A. L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595.
23. Dieck, H. A.; Heck, F. R. J. Organometal. Chem. 1975, 93, 259.
24. Ferraz, H. M. C.; Comasseto, J. V.; Brandt, C. A. Magn. Reson. Chem. 1987, 25, 42.
25. Yoshimatsu, M.; Hasegawa, J. J. Chem. Soc., Perkin Trans. 1 1997, 211.
26. Yoshimatsu, M.; Kawahigashi, M.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1995, 583.
27. Marcuzzi, F.; Azzena, U.; Melloni, G. J. Chem. Soc., Perkin Trans. 1 1993, 2957.