Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5- diyne derivatives via an addition-elimination reaction

Journal of Fluorine Chemistry

Volumn 156, Issue , 2013, Pages 144-151

  Konno, Tsutomu ^a   Kishi, Misato ^a   Ishihara, Takashi ^a   Yamada, Shigeyuki ^b  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Addition elimination reaction; Alkynyllithiums; Fluorinated alkenes; Fluorine containing enyne compounds; Fluoroalkylated enediyne compounds

Indexed keywords

EID: 84886125322     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2013.09.010     Document Type: Article

References (30)

1. U. Galm, M.H. Hager, S.G. Van Lanen, J. Ju, J.S. Thorson, and B. Shen Chem. Rev. 105 2005 739 758
2. R.G. Bergman Acc. Chem. Res. 6 1973 25 31
3. R.R. Jones, and R.G. Bergman J. Am. Chem. Soc. 94 1972 660 661
4. S. Caddick, V.M. Delisser, V.E. Doyle, S. Khan, A.G. Avent, and S. Vile Tetrahedron 55 1999 2737 2754
5. K.K. Wang Chem. Rev. 96 1996 207 222
6. K.C. Nikolaou, and A.L. Smith Acc. Chem. Res. 25 1992 497 503
7. C.A. Landis, M.M. Payne, D.L. Eaton, and J.E. Anthony J. Am. Chem. Soc. 126 2004 1338 1339
8. J.L. Scott, S.R. Parkin, and J.E. Anthony Synlett 2004 161 165
9. D.M. Bowles, G.J. Palmer, C.A. Landis, J.L. Scott, and J.E. Anthony Tetrahedron 57 2001 3753 3760
10. S.-Y. Chow, G.J. Palmer, D.M. Bowles, and J.E. Anthony Org. Lett. 2 2000 961 963
11. D.M. Bowles, and J.E. Anthony Org. Lett. 2 2000 85 87
12. S. Yamada, T. Konno, T. Ishihara, and H. Yamanaka J. Fluorine Chem. 126 2005 125 133
13. F. Hong, and C.M. Hu Chin. Chem. Lett. 6 1995 279 280
14. H.H. Jeon, J.B. Son, J.H. Choi, and I.H. Jeong Tetrahedron Lett. 48 2007 627 631
15. M. Shimizu, T. Fujimoto, X. Liu, H. Minezaki, T. Hata, and T. Hiyama Tetrahedron 59 2003 9811 9823
16. M. Shimizu, T. Fujimoto, H. Minezaki, T. Hata, and T. Hiyama J. Am. Chem. Soc. 123 2001 6947 6948
17. D. O'Hagen Chem. Soc. Rev. 37 2008 308 319
18. J.-P. Bégué, and D. Bonnet-Delpon J. Fluorine Chem. 127 2006 992 1012
19. S. Yamamoto, K. Matsuda, and M. Irie Org. Lett. 5 2003 1769 1772
20. T. Kaieda, S. Kobatake, H. Miyasaka, M. Murakami, N. Iwai, Y. Nagata, A. Itaya, and M. Irie J. Am. Chem. Soc. 124 2002 2015 2024
21. M. Irie Chem. Rev. 100 2000 1685 1716
22. T. Hiyama Organofluorine Compounds. Chemistry and Applications 2000 Springer New York
23. J.P. Bégué, D. Bonnet-Delpon, D. Mexureur, and M. Ourévitch Mag. Reson. Chem. 29 1991 675 678
24. S. Yamada, T. Takahashi, T. Konno, and T. Ishihara J. Fluorine Chem. 149 2013 95 103
25. S. Yamada, K. Shimoji, T. Takahashi, T. Konno, and T. Ishihara Chem. Asian J. 5 2010 1846 1853
26. S. Yamada, E. Ishii, T. Konno, and T. Ishihara Tetrahedron 64 2008 4215 4223
27. S. Yamada, M. Noma, K. Hondo, T. Konno, and T. Ishihara J. Org. Chem. 73 2008 522 528
28. S. Yamada, E. Ishii, T. Konno, and T. Ishihara Org. Biomol. Chem. 5 2007 1442 1449
29. S. Yamada, T. Takahashi, T. Konno, and T. Ishihara Chem. Commun. 2007 3679 3681
30. T. Konno, J. Chae, M. Kanda, G. Nagai, K. Tamura, T. Ishihara, and H. Yamanaka Tetrahedron 59 2003 7571 7580