Construction of highly substituted stereodefined dienes by cross-coupling of α-allenic acetates

European Journal of Organic Chemistry

Volumn , Issue 1, 2007, Pages 40-43

  Schneekloth Jr , John S ^a   Pucheault, Mathieu ^a   Crews, Craig M ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Alkenes; Allenes; Cross coupling

Indexed keywords

EID: 33846054922     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600721     Document Type: Article

References (26)

1. M. Ishibashi, Y. Ohizumi, M. Hamashima, H. Nakamura, Y. Hirata, T. Sasaki, J. Kobayashi, J. Chem. Soc., Chem. Commun. 1987, 1127-1129.
2. H. Achenbach, A. Muhlenfeld, H. Zahner, Tetrahedron Lett. 1985, 26, 6167-6170.
3. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
4. J. Tsuji, Palladium Reagents and Catalysts: Innovations, in: Organic Synthesis John Wiley and Sons, Chinchester, 1995, p. 560.
5. Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 517.
6. M. B. Cid, G. Pattenden, Tetrahedron Lett. 2000, 41, 7373-7378.
7. J. J. Eshelby, P. J. Parsons, N. C. Sillars, P. J. Crowley, J. Chem. Soc., Chem. Commun. 1995, 1497-1498.
8. A. K. Mandal, J. S. Schneekloth, C. M. Crews, Org. Lett. 2005, 7, 3645-3648.
9. A. K. Mandal, J. S. Schneekloth, K. Kuramochi, C. M. Crews, Org. Lett. 2006, 8, 427-430.
10. T. Moriya, T. Furuuchi, N. Miyaura, A. Suzuki, Tetrahedron 1994, 50, 7961-7968.
11. H. Kleijn, H. Wertmijze, J. Meijer, P. Vermeer, Recl. Trav. Chim. Pays-Bas 1983, 102, 378-380.
12. J. Nokam, A. Maihara, J. Tsuji, Tetrahedron Lett. 1990, 31, 5629-5630.
13. B. M. Trost, D. R. Fandrick, D. C. Dinh, J. Am. Chem. Soc. 2005, 127, 14186-14187.
14. D. Djahanbini, B. Cazes, J. Gore, Tetrahedron 1987, 43, 3441-3452.
15. S. M. Ma, Chem. Rev. 2005, 105, 2829-2871 and references cited therein.
16. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067-3125, and references therein.
17. a) J. Tsuji, H. Takahashi, M. Morikawa, Tetrahedron Lett. 1965, 6, 4387-4388;
18. b) B. M. Trost, T. J. Fullerton, J. Am. Chem. Soc. 1973, 95, 292-294.
19. For a review: c) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
20. a) E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823.
21. For a review: b) E.-I. Negishi, in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chapter 1;
22. c) E. Erdik, Tetrahedron 1992, 48, 9577-9648.
23. A. Horvath, J. E. Bäckvall, J. Org. Chem. 2001, 66, 8120-8126.
24. Ligands were purchased from Strem Chemicals or Aldrich Chemicals.
25. Organozinc reagents were purchased from Aldrich Chemicals.
26. M. C. Harris, O. Geis, S. L. Buchwald, J. Org. Chem. 1999, 64, 6019-6022.