Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 14, 1996, Pages 1741-1747

  Zhi, Chengxin ^a   Chen, Qing Yun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748891218     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960001741     Document Type: Article

References (70)

1. A. O. Mascaretti, Aldrichim. Acta, 1993, 26, 47;
2. G. Resnati, Tetrahedron, 1993, 49, 9385;
3. J. A. Wilkinson, Chem. Rev., 1992, 92, 505;
4. P. Bravo and G. Resnati, Tetrahedron: Asymmetry, 1990, 1, 661;
5. D. Seebach, Angew. Chem., Int. Ed. Engl., 1990, 29, 1320;
6. J. T. Welch, Tetrahedron, 1987, 43, 3123;
7. J. Mann, Chem. Soc. Rev. 1987, 16, 381;
8. R. Filler and Y. Kobayashi, Biomedicinal Aspects of Fluorine Chemistry, Elsevier Biomedical Press, New York, 1982.
9. J. F. Liebman, A. Greenberg and W. R. Dolbier, Fluorine-Containing Molecules: Structure, Reactivity, Synthesis and Applications, VCH, New York, 1988, ch. 11.
10. (a) S. Rozan and R. Filler, Tetrahedron, 1985, 41, 1111;
11. (b) H. Nakai, N. Hamanka, H. Miyake and M. Hayashi, Chem. Lett., 1979, 1499;
12. (c) Y. Kobayashi, T. Taguchi, T. Terada, J. Oshida, M. Morisaki and N. Ikekawa, J. Chem. Soc., Perkin Trans. 1, 1982, 85;
13. (d) M. Okabe, R.-C. Sun and G. B. Zenchoff. J. Org. Chem., 1991, 56, 4392;
14. (e) M. A. Siddiqui, V. E. Marquez, J. S. Drisoll and J. J. Barchi, Jr., Tetrahedron Lett., 1994, 35, 3263;
15. (f) T. Yamazaki, T. Yamamoto and T. Kitazume, J. Org. Chem., 1989, 54, 83.
16. J. Bomelburg, G. Heppke and A. Ranft, Z. Naturforsch. Teil B, 1989, 44, 1127.
17. R. Buchecker, S. M. Kelly and J. Funfschilling, Liq. Cryst., 1990, 8, 217;
18. D. M. Walba, H. A. Razavi, N. A. Clark and D. S. Parmar, J. Am. Chem. Soc., 1988, 110, 8686;
19. H. Nohira, S. Nakamura and M. Kamei, Mol. Cryst. Liq. Cryst., 1990, 180B, 379;
20. N. S. Nakamura and M. H. Nohira, Mol. Cryst. Liq. Cryst., 1990, 185, 199.
21. S. Arakawa, K. Nito and J. Seto, Mol. Cryst. Liq. Cryst., 1991, 204, 15.
22. E. D. Bergmann and I. Blank, J. Chem. Soc., 1953, 3786;
23. N. J. M. Birdsall, Tetrahedron Lett., 1971, 2675;
24. N. Ishikawa, T. Kitazume, T. Yamazaki, Y. Mochida and T. Tatsuno, Chem. Lett., 1981, 761;
25. S. A. Pogany, G. M. Zentner and C. D. Ringeisen, Synthesis, 1987, 718.
26. E. D. Bergmann and S. Szinai, J. Chem. Soc., 1956, 1521.
27. W. J. Middleton, J. Org. Chem., 1975, 40, 574;
28. G. Lowe and B. V. L. Potter, J. Chem. Soc., Perkin Trans. 1, 1980, 2029;
29. A. Takaoka, H. Iwakiri and N. Ishikawa, Bull. Chem. Soc. Jpn., 1979, 52, 3377.
30. D. J. Costa, N. E. Boulin and J. G. Riess. Tetrahedron, 1974, 30, 3793.
31. F. Faustini, S. DeMunari, A. Panzeri, V. Villa and C. A. Gandolfi, Tetrahedron Lett., 1981, 22, 4533;
32. R. Keck and J. Retey, Helv. Chim. Acta, 1980, 63, 769;
33. S. Hamman, M. Barrelle and F. Tetaz, J. Fluorine Chem., 1987, 37, 85.
34. (a) E. Differding and H. Ofner, Synlett. 1991, 187;
35. (b) Y. Takeuchi, K. Nagata and T. Koizumi, J. Org. Chem., 1989, 54, 5453;
36. (c) A. F. Davis, P. Zhou and C. K. Murphy, Tetrahedron Lett., 1993, 34, 3971;
37. (d) T. Tsushima, K. Kawada, T. Tsuji and S. Misaki, J. Org. Chem., 1982, 47, 1107;
38. S. Rozen, O. Lerman and M. Kol, (e) J. Chem. Soc., Chem. Commun., 1981, 443;
39. (f) J. Org. Chem., 1985, 50, 4753;
40. (g) S. T. Purrington and W. A. Jones, J. Org. Chem., 1983, 48, 761;
41. (h) W. E. Barnette, Am. Chem. Soc., 1984, 106, 452;
42. (i) F. A. Davis and W. Man, Tetrahedron Lett., 1992, 33, 1153.
43. W. J. Middleton and E. M. Bingham. J. Am. Chem. Soc., 1980, 102, 4845;
44. S. T. Purrington and D. L. Woodard, J. Org. Chem., 1990, 55, 3423.
45. (a) E. T. McBee, O. R. Pierce and D. L. Christman, J. Am. Chem. Soc., 1955, 77, 1581;
46. (b) S. Brandange, O. Dahlman and L. Morch, J. Am. Chem. Soc., 1981, 103, 4452;
47. (c) R. J. Linderman and D. M. Graves. J. Org. Chem., 1989, 54, 661;
48. (d) Y. Shen and M. Qi. J. Chem. Res.(S), 1993, 222.
49. M. Saburi, L. M. Shao and T. Sakurai, Tetrahedron Lett., 1992, 33, 7877;
50. T. Kitazume and N. Ishikawa, Chem. Lett., 1983, 237.
51. A. Thenappan and D. J. Burton, J. Org. Chem., 1991, 56, 273;
52. Tetrahedron Lett., 1989, 30, 6113;
53. J. Org. Chem., 1990, 55, 2311;
54. Tetrahedron Lett., 1989, 30, 3641.
55. Y. Wang, Z. Y. Yang and D. J. Burton, Tetrahedron Lett., 1992, 33, 2137.
56. B. Englund. Org. Synth., 1963, Coll. Vol. IV, p. 423.
57. N. O. Brace, J. Am. Chem. Soc., 1962, 84, 3020.
58. Q. Y. Chen, Y. B. He and Z. Y. Yang, J. Fluorine Chem., 1986, 34, 255;
59. Q. Y. Chen and Z. Y. Yang, J. Fluorine Chem., 1985, 28, 399.
60. A. L. J. Beckwith, C. J. Easton, T. Lawrence and A. K. Serelis. Aust. J. Chem., 1983, 36, 545.
61. Z. Y. Yang and D. J. Burton, J. Org. Chem., 1991, 56, 5125.
62. W. E. Truce and G. C. Wolf. J. Org. Chem., 1971, 36, 1727.
63. (a) I. D. Peter, Tetrahedron. 1995, 51, 7579;
64. (b) Y. Ding, G. Zhao and W. Y. Huang, Tetrahedron Lett., 1992, 33, 8119;
65. (c) C. M. Hu and Y. L. Qiu, J. Org. Chem., 1992, 57, 3339;
66. C. M. Hu and J. Chen, (d) J. Chem. Soc., Perkin Trans. 1, 1993, 327;
67. (e) J. Chem. Soc., Chem. Commun. 1993, 72.
68. P. Laurent, H. Blancou and A. Commeyras. Synthesis, 1993, 77.
69. M. Nagano, J. Sakai, M. Mizukai, N, Nakamura, E. Misaka, S. Kobayashi and K. Tomito, Jap. Pat., 79 73 772 1979 (Chem. Ahstr., 1979, 91, 211401).
70. E. T. McBee, D. L. Christman, R. W. Johnson, Jr., and C. W. Roberts. J. Am. Chem. Soc., 1956, 78, 4595.