Ethyl 3-Fluoro-3-(tributylstannyl)-2-me-thoxyacrylate: Preparation and Palladium/ Copper-Cocatalyzed Cross-Coupling Reactions as a Novel Route to β-Fluoro-a-keto Acid Derivatives

Journal of Organic Chemistry

Volumn 60, Issue 20, 1995, Pages 6608-6611

  Shi, Guo Qiang ^a   Cao, Zhi Yao ^a   Zhang, Xiao Bing ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000576292     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00125a060     Document Type: Article

References (45)

1. For a review on the syntheses and properties of a-keto acid derivatives, see: Cooper, A. J. L.; Ginos, J. Z.; Meister, A. Chem. Rev. 1983, 83, 321.
2. Filler, R., Kobayashi, Y., Eds. Biomedicinal Aspects of Fluorine Chemistry, Elsevier: Amsterdam, 1982.
3. Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry, John Wiley & Sons: New York, 1990.
4. Filler, R., Kobayashi, Y., Yagupolski, L. M., Eds. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier Science: Amsterdam, 1993.
5. Kollonitsh, J.; Perkins, L. M.; Patchett, A. A.; Doldouras, G. A.; Marburg, S.; Duggan, D. E.; Maycock, A. L.; Aster, S. D. Nature 1978, 274, 906.
6. Walsh, C. Tetrahedron 1982, 38, 871.
7. Bey, P. Ann. Chim. Fr. 1984, 9, 695.
8. Kollonitsh, J. Israel J. Chem. 1978, 17, 53.
9. Kawada, K.; Tsushima, T. Kagaku Kogyo 1987, 38, 164;
10. Chem. Abstr. 1987, 107, R97067.
11. Kukhar, V. P. J. Fluorine Chem. 1994, 69, 199.
12. Tsushima, T.; Kawada, K.; Tsuji, T. J. Org. Chem. 1982, 47, 1107.
13. Tsushima, T.; Kawada, K.; Nishikawa, J.; Sato, T.; Tori, K.; Tsuji, T. J. Org. Chem. 1984, 49, 1163.
14. Ayi, A. I.; Remli, M. R.; Condom, R.; Geudj, R. J. Fluorine Chem. 1981, 17, 565.
15. Remli, M.; Ayi, A. I.; Guedj, R. J. Fluorine Chem. 1982, 20, 677.
16. Recent findings: Reetz, M. T.; Heimbach, H.; Schwellnus, K. Tetrahedron Lett. 1984, 25, 511.
17. Home, D.; Gaudino, J.; Thompson, W. J. Tetrahedron Lett. 1984, 25, 3529.
18. Tanaka, M.; Kobayashi, T.; Sakakura, T. J. Chem. Soc., Chem. Commun. 1985, 837.
19. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1987, 28, 3039.
20. Mikolajczyk, M.; Midura, W. H. Synlett 1991, 245.
21. Sagimura, H.; Yoshida, K. Bull. Chem. Soc. Jpn. 1992, 65, 3209.
22. Barton, D. H. R.; Chern, C.-Y.; Jaszberenyi, J. C. S. Tetrahedron 1995, 51, 1867.
23. Shi, G.-Q.; Cai, W.-L. Submitted for publication.
24. Piers, E.; Wong, T.; Ellis, K. A. Can. J. Chem. 1992, 70, 2058.
25. Seitz, D. E.; Lee, S.-H. Tetrahedron Lett. 1981, 22, 4909.
26. Reviews: Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
27. Mitchell, T. N. Synthesis 1992, 803.
28. For representative examples, see: Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983,48, 4634.
29. Stille, J. K.; Groh, B. L. J. Org. Chem. 1987,109, 813.
30. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557.
31. Houpis, I. N.; DiMichele, L.; Molina, A. Synlett 1993, 365.
32. Lai, M.-T.; Li, D.; Oh, E.; Liu, H.-W. J. Am. Chem. Soc. 1993, 115, 1619.
33. F-C=O)) for compound 7a is 10 Hz which may be considered to be indicative of a trans relationship between the two nuclei. For reference, see: Ichikawa, J.; Yokota, N.; Kobayashi, M.; Minami, T. Synlett 1993, 186.
34. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905 and references cited therein.
35. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
36. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
37. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
38. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
39. Olah, G. A.; Narang, S. C. Tetrahedron 1982, 38, 2225.
40. Kauffman, G. B.; Fang, L. Y. Inorg. Synth. 1983, 22, 101.
41. Knunyants, I. L.; Shokina, V. V.; Tyuleneva, V. V. Dokl. Akad. Nauk. SSSR 1966, 169, 594;
42. Chem. Abstr. 1966, 65, 15218e.
43. Sianesi, D.; Pasetti, A.; Tarli, F. J. Org. Chem. 1966, 31, 2312. This compound was also prepared in our laboratory by another convenient method:
44. Francese, C.; Toxdeux, M.; Wakselman, C. Tetrahedron Lett. 1988, 29, 1029.
45. Shi, G.-Q.; Xu, Y.-Y. J. Chem. Soc., Chem. Commun. 1989, 607.