A highly efficient, selective, and general method for the synthesis of conjugated (all-E)-oligoenes of the (CH=CH)n type via iterative hydrozirconation-palladium-catalyzed cross-coupling

Organic Letters

Volumn 4, Issue 5, 2002, Pages 703-706

  Zeng, Fanxing ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BIOLOGICAL FACTOR; MACROLIDE; PALLADIUM; POLYENE; ZIRCONIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BIOLOGICAL FACTORS; CATALYSIS; MACROLIDES; PALLADIUM; POLYENES; STEREOISOMERISM; ZIRCONIUM;

EID: 0037035007     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0102794     Document Type: Article

References (23)

1. 2OEt, see: Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
2. Lipshutz, B. H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555.
3. Zeng, F.; Negishi, E. Org. Lett. 2001, 3, 719.
4. 3SiC≡ CZnCl with a mixture of (E)-and (Z)-1,2-dibromoethylene had been previously reported (Carpita, A.; Rossi, R. Tetrahedron lett. 1986, 27,
5. For a review, see: Zweifel, G.; Miller, J. A. Org. React. 1984, 32, 375.
6. Brown, H. C. Organic Syntheses via Boranes; John Wiley & Sons: New York, 1975; p 283.
7. Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115.
8. (a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Commun. 1977, 683.
9. (b) Kotora, M.; Xu, C.; Negishi, E. J. Org. Chem. 1997, 8957.
10. (a) Boschelli, D.; Takemasa, T.; Nishitani, Y.; Masamune, S. Tetrahedron Lett. 1985, 26, 5239.
11. (b) Nicolaou, K. C.; Chakraborty, T. K.; Daines, R. A.; Simpkins, N. S. J. Chem. Soc., Chem. Commun. 1986, 413.
12. (c) Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K. J. Am. Chem. Soc. 1987, 109, 2208.
13. (d) Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc. 1988, 110, 4672.
14. (e) Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1988, 110, 4685.
15. Ciufolini, M. A.; Zhu, S.; Deaton, M. V. J. Org. Chem. 1997, 62, 7806.
16. Romo, D.; Johnson, D. D.; Plamondon, L.; Miwa, T.; Schreiber, S. L. J. Org. Chem. 1992, 57, 5060.
17. Weir, J. R.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1980, 45, 4926.
18. Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616.
19. For some seminal contributions on the Pd-catalyzed conjugate substitution, see: (a) Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729.
20. (b) See ref 8a.
21. (c) Okukado, N.; Van Horn, D. E.; Klima, W. L.; Negishi, E. Tetrahedron Lett. 1978, 1027.
22. (d) Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 700, 2254.
23. (e) Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223.