Acylation of in situ generated trimethylsilyl diethylphosphonoacetate using magnesium chloride-triethylamine: A practical synthesis of β-keto phosphonates

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 9, 1997, Pages 1361-1363

  Kim, Dae Young ^a   Kong, Myeon Sik ^a   Lee, Kilsung ^b  

^a Soonchunhyang University   (South Korea)

^b Samsung Chemical Technology Center   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748665505     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a607683a     Document Type: Article

References (62)

1. For general reviews, see: B. E. Maryanoff and A. B. Beitz, Chem. Rev., 1989, 89, 863;
2. W. S. Wadsworth, Jr., Org. React. (N. Y.), 1977, 25, 73;
3. B. J. Walker, Organophosphorus Reagents in Organic Synthesis, ed. J. I. G. Cadogan, Academic Press, New York, 1974, pp. 155-206;
4. S. Kelly, Alkene Synthesis, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and S. Schreiber, Pergamon Press, Oxford. 1991, vol. 1, pp. 755-781.
5. (a) F. W. Lichtenthaler, Chem. Rev., 1961, 61, 607;
6. (b) M. Honda, T. Katsuki and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 3857;
7. (c) B. Crobel, L. Medinger, J. P. Haelters and G. Sturtz, Synthesis, 1985, 1048;
8. (d) M. Kitamura, M. Tokunaga and R. Noyori, J. Am. Chem. Soc., 1995, 117, 2931;
9. (e) C. Yuan and R. Xie, Phosphorus and Sulfur, 1994, 90, 47.
10. E. J. Corey and G. T. Kwiatkowski, J. Am. Chem. Soc., 1966, 88, 5654;
11. P. Coutrout, P. Savignac and F. Mathay, Synthesis, 1978, 36;
12. E. E. Aboujaoude, N. Colligan and P. Savignac, J. Organomet. Chem., 1984, 264, 9;
13. D. E. Rudisill and J. P. Whitten, Synthesis, 1994, 851;
14. K. Narkunam and M. Nagarajan, J. Org. Chem., 1994, 59, 6386;
15. M. Mikolajczyk and M. Mikine, J. Org. Chem., 1994, 59, 6760.
16. (a) R. D. Clark, L. G. Kozar and C. H. Heathcock, Synthesis, 1975, 635;
17. (b) P. A. Grieco and C. S. Pogonowski, J. Am. Chem. Soc., 1973, 95, 3071;
18. (c) F. Mathey and P. Savignac, Synthesis, 1976, 766;
19. (d) P. Savignac and F. Mathey, Tetrahedron Lett., 1976, 17, 2829;
20. (e) F. Mathey and P. Savignac, Tetrahedron, 1978, 649;
21. (f) E. Aboujaoude, N. Colligan, M. P. Teulade and P. Savignac, Phosphorus and Sulfur, 1985, 25, 57.
22. P. D. Theisen and C. H. Heathcock, J. Org. Chem., 1988, 53, 2374.
23. K. Lee and D. Y. Oh, Bull. Korean Chem. Soc., 1989, 10, 613;
24. K. Lee and D. Y. Oh, Synth. Commun., 1991, 21, 279.
25. K. Lee and D. F. Wiemer, J. Org. Chem., 1991, 56, 5556;
26. T. Calogeropoulou, G. B. Hammond and D. F Wiemer J. Org. Chem., 1987, 52, 4185;
27. Y. Z. An and D. F Wiemer, J. Org. Chem., 1992, 57, 317;
28. Y. Z. An. J. G. An and D. F. Wiemer, J. Org. Chem., 1994, 59, 8197.
29. S. Hong, K. Chang, B. Ku and D. Y. Oh, Tetrahedron Lett., 1989, 30, 3307.
30. R. K. Boeckman, Jr., M. A. Walters and H. Koyano, Tetrahedron Lett., 1989, 30, 4787.
31. P. Coutrot and A. Ghribi, Synthesis, 1986, 661.
32. O. Tsuga, S. Kanemasa, H. Suga and N. Nakagawa, Chem. Lett., 1986, 60, 2463;
33. O. Tsuga, S. Kanemasa, H. Suga and N. Nakagawa, Bull. Chem. Soc. Jpn., 1987, 60, 2463;
34. S. Kanemasa, N. Nakagawa, H. Suga and O. Tsuge, Bull. Chem. Soc. Jpn., 1989, 69, 171.
35. M. M. Kabat, Tetrahedron Lett., 1993, 34, 8543;
36. H. J. Altenbach and R. Dorff, Tetrahedron Lett., 1981, 22, 5175.
37. E. Ohler, H. S. Kang and E. Zbiral, Synthesis, 1988, 623.
38. Y. J. Koh and D. Y. Oh, Tetrahedron Lett., 1993, 34, 2147.
39. T. Gasteiger and C. Herzig, Tetrahedron Lett., 1980, 21, 2687;
40. C. Herzig and T. Gasteiger, Chem. Ber., 1982, 115, 601.
41. D. Y. Kim and M. S. Kong, J. Chem. Soc., Perkin Trans. 1, 1994, 3359.
42. K. C. Nicolaou, S. P. Seitz, M. R. Pavia and N. A. Petasis, J. Org. Chem., 1979, 44, 4011;
43. K. C. Nicolaou, M. R. Pavia and S. P. Seitz, J. Am. Chem. Soc., 1981, 103, 1224;
44. M. Lim and V. E. Marquez, Tetrahedron Lett., 1983, 24, 4051;
45. M. Mikolajczyk and P. Balczewski, Synthesis, 1984, 691.
46. D. Y. Kim, J. Y. Mang and D. Y. Oh, Synth. Commun., 1994, 24, 629.
47. S. M. Ruder and V. R. Kulkarni, Synthesis, 1993, 945;
48. S. R. Ruder and V. R. Kulkarni, J. Chem. Soc., Chem. Commun., 1994, 2119.
49. D. Y. Kim, M. S. Kong and D. Y. Rhie, Synth. Commun., 1995, 25, 2865;
50. D. Y. Kim, M. S. Kong and T. H. Kim, Synth. Commun., 1996, 26, 2487;
51. B. Corbel, I. L. Hostis-Kervella and J. P. Haelters, Synth. Commun., 1996, 26, 2561.
52. D. Y. Kim, K. Lee and D. Y. Oh, J. Chem. Soc., Perkin Trans. 1, 1992, 2451;
53. D. Y. Kim, J. Y. Mang, J. W. Lee and D. Y. Oh, Bull. Korean Chem. Soc., 1993, 14, 526.
54. The combination of magnesium and triethylamine provides a useful base system for metallating diethyl malonate derivatives, see: M. W. Rathke and P. J. Cowan, J. Org. Chem., 1985, 50, 2622;
55. M. W. Rathke and M. A. Nowak, Synth. Commun., 1985, 15, 1039;
56. D. L. Kuo, Tetrahedron Lett., 1992, 42, 9233;
57. D. J. Krysan, Tetrahedron Lett., 1996, 37, 3303;
58. D. Y. Kim, D. Y. Rhie and D. Y. Oh, Tetrahedron Lett., 1996, 37, 653.
59. Diethylphosphonoacetic acid can be prepared by the Arbuzov reaction or by the hydrolysis of triethyl phosphonoacetate. For example, see: P. Coutrot, M. Snoussi and P. Savignac, Synthesis, 1978, 133;
60. L. Lombarde and R. J. K. Taylor, Synthesis, 1978, 131;
61. S. Katusumura and S. Isoe, Chem. Lett., 1982, 1689;
62. L. Lombard and R. J. K. Taylor, Synth. Commun., 1978, 8, 463.