An efficient one-pot synthesis of new polyfunctional phosphorus acid amphiphiles

European Journal of Organic Chemistry

Volumn , Issue 2, 2000, Pages 281-289

  Vercruysse, Karine ^a   Déjugnat, Christophe ^a   Munoz, Aurelio ^a   Etemad Moghadam, Guita ^a  

^a Université Paul Sabatier   (France)

Author keywords

( Aminoalkyl)phosphonic acids; Carboxyalkyl ( aminoalkyl)phosphonic acid monoesters; Phosphorus acid amphiphiles; Pudovik reaction; Spirophosphorane

Indexed keywords

AMPHOPHILE; PHOSPHORUS ACID DERIVATIVE;

ARTICLE; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0043189097     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200001)2000:2<281::AID-EJOC281>3.0.CO;2-2     Document Type: Article

References (80)

1. A. Kalir, H. H. Kalir, The Chemistry of Organophosphorus Compounds (Ed.: F. R. Hartley), Wiley & Sons, New York, 1996, vol. 4, pp. 767-780.
2. [2a] H. R. Hudson, M. Pianka, Phosphorus Sulfur Silicon Relat. Elem. 1996, 109-110, 345-348.
3. [2b] L. Maier, P. J. Diel, Phosphorus Sulfur Silicon Relat. Elem. 1994, 90, 259-279.
4. [3a] C. Gerber, D. Seebach, Helv. Chim. Acta 1991, 74, 1373-1385 and references cited therein.
5. [3b] B. Stowasser, K. H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett. 1992, 33, 6625-6628.
6. [3c] S. A. Beers, C. F. Schwender, D. A. Loughney, E. Malloy, K. Demarest, J. Jordan, Bioorg. Med. Chem. 1996, 4, 1693-1701.
7. L. S. Hollis, A. V. Miller, A. R. Amundsen, J. E. Schurig, E. W. Stern, J. Med. Chem. 1990, 33, 105-111.
8. J. G. Dingwall, Phosphorus Sulfur 1983, 18, 353-356.
9. J. A. Mikroyannidis, Phosphorus Sulfur 1982, 12, 249-258.
10. [7a] B. Song, D. Chen, M. Bastian, R. B. Martin, H. Sigel, Helv. Chim. Acta 1994, 77, 1738-1756.
11. [7b] Th. J. Einhäuser, M. Galanski, E. Vogel, B. K. Keppler, Inorg. Chim. Acta 1997, 257, 265-268.
12. R. S. Edmundson, The Chemistry of Organophosphorus Compounds (Ed.: F. R. Hartley), Wiley & Sons, New York, 1996, vol. 4, pp. 293-396.
13. [9a] L. Maier, H. Spörri, Phosphorus Sulfur Silicon Relat. Elem. 1991, 61, 69-75.
14. [9b] B. Dhawan, D. Redmore, Phosphorus Sulfur 1987, 32, 119-144.
15. [9c] E. K. Baylis, C. D. Campbell, J. G. Dingwall, J. Chem. Soc., Perkin Trans. 1 1984, 2845-2853.
16. [10a] A. Heisler, C. Rabiller, R. Douillard, N. Goalou, G. Hägele, F. Levayer, Tetrahedron: Asymmetry 1993, 4, 959-960.
17. [10b] F. Wuggenig, F. Hammerschmidt, Monatsh. Chem. 1998, 129, 423-436.
18. [11a] O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 1998, 9, 1279-1332 and references cited therein.
19. [11b] Y. L. Bennani, S. Hanessian, Chem. Rev. 1997, 97, 3161-3195 and references cited therein.
20. [11c] C. Yuan, S. Li, C. Li, S. Chen, W. Huang, G. Wang, C. Pan, Y. Zhang, Heteroatom Chem. 1997, 8, 103-122.
21. [11d] V. P. Kukhar, V. A. Soloshonok, V. A. Solodenko, Phosphorus Sulfur Silicon Relat. Elem. 1994, 92, 239-264.
22. [12a] I. M. Lefebvre, S. A. Evans, Jr., J. Org. Chem. 1997, 62, 7532-7533.
23. [12b] C. K. McClure, P. K. Mishra, C. W. Grote, J. Org. Chem. 1997, 62, 2437-2441.
24. [12c] C. Maury, Q. Wang, T. Gharbaoui, M. Chiadmi, A. Tomas, J. Royer, H.-P. Husson, Tetrahedron 1997, 53, 3627-3636.
25. [13a] M. L. Bojin, S. A. Evans, Jr., Phosphorus Sulfur Silicon Relat. Elem. 1996, 111, 157.
26. [13b] M. Seki, K. Kondo, T. Iwasaki, J. Chem. Soc., Perkin Trans. 1 1996, 3-5.
27. [13c] A. B. Smith, III, K. M. Yager, C. M. Taylor, J. Am. Chem. Soc. 1995, 117, 10879-10888.
28. [14a] T. Yokomatsu, S. Shibuya, Tetrahedron: Asymmetry 1992, 3, 377-378.
29. [14b] S. E. Denmark, N. Chatani, S. V. Pansare, Tetrahedron 1992, 48, 2191-2208.
30. [14c] D. Y. Kim, D. Y. Rhie, Tetrahedron 1997, 53, 13603-13608.
31. [14d] H. J. Cristau, J. M. Lambert, A. Sarris, J. L. Pirat, Phosphorus Sulfur Silicon Relat. Elem. 1996, 111, 125.
32. [15a] A. N. Pudovik, I. V. Konovalova, Synthesis 1979, 81-96.
33. [15b] L. Cottier, G. Descotes, G. Gonera, G. Grabowski, J. Lewkowski, R. Skowronski, Phosphorus Sulfur Silicon Relat. Elem. 1996, 118, 181-188.
34. [15c] H. Sasai, S. Arai, Y. Tahara, M. Shibasaki, J. Org. Chem. 1995, 60, 6656-6657.
35. [15d] S. Failla, P. Finocchiaro, Phosphorus Sulfur Silicon Relat. Elem. 1995, 105, 195-203.
36. [15e] C. Yuan, S. Li, G. Wang, Y. Ma, Phosphorus Sulfur Silicon Relat. Elem. 1993, 81, 27-35.
37. [16a] S. W. A. Bligh, C. M. McGrath, S. Failla, P. Finocchiaro, Phosphorus Sulfur Silicon Relat. Elem. 1996, 118, 189-194 and references cited therein.
38. [16b] B. Boduszek, Tetrahedron 1996, 52, 12483-12494.
39. [16c] A. Holy, Synthesis 1998, 381-385.
40. [17a] D. Semenzin, G. Etemad-Moghadam, D. Albouy, M. Koenig, Tetrahedron Lett. 1994, 35, 3297-3300.
41. [17b] D. Semenzin, G. Etemad-Moghadam, D. Albouy, O. Diallo, M. Koenig, J. Org. Chem. 1997, 62, 2414-2422.
42. [17c] D. Albouy, M. Laspéras, G. Etemad-Moghadam, M. Koenig, Tetrahedron Lett. 1999, 40, 2311-2314.
43. [17d] D. Albouy, G. Etemad-Moghadam, M. Koenig, Eur. J. Org. Chem. 1999, 861-867.
44. [18a] C. Hubert, B. Oussaid, G. Etemad-Moghadam, M. Koenig, B. Garrigues, Synthesis 1994, 51-55.
45. [18b] C. Hubert, A. Munoz, B. Garrigues, J. L. Luche, J. Org. Chem. 1995, 60, 1488-1489.
46. D. Albouy, A. Brun, A. Munoz, G. Etemad-Moghadam, J. Org. Chem. 1998, 63, 7223-7230.
47. T. Aoyagi, M. Yamamura, K. Matsui, Y. Nagase, Drug Des. Discov. 1991, 8, 47-56.
48. [21a] I. S. Antipin, I. I. Stoikov, A. R. Garifzyanov, A. I. Konovalov, Phosphorus Sulfur Silicon Relat. Elem. 1996, 111, 117.
49. [21b] P. Wieczorek, J. A. Jönsson, L. Mathiasson, Anal. Chim. Acta 1997, 346, 191-197.
50. [22a] S. W. A. Bligh, N. Choi, S. Failla, P. Finocchiaro, A. Il'yasov, M. Libertini, C. M. McGrath, M. McPartlin, T. M. Woodroffe, J. Chem. Soc., Dalton Trans. 1994, 3333-3334.
51. [22b] Y. Zhang, A. Clearfield, Inorg. Chem. 1992, 31, 2821-2826.
52. [22c] C. T. Seip, G. E. Granroth, M. W. Meisel, D. R. Talham, J. Am. Chem. Soc. 1997, 119, 7084-7094.
53. [22d] D. R. Talham, C. T. Seip, S. Whipps, G. E. Fanucci, M. A. Petruska, Comments Inorg. Chem. 1997, 19, 133-151.
54. [23a] R. Burgada, R. Setton, The Chemistry of Organophosphorus Compounds (Ed.: F. R. Hartley), Wiley & Sons, New York, 1994, vol. 3, pp. 185-272, and references cited therein.
55. [23b] R. R. Holmes, A. Chandrasekaran, R. O. Day, D. J. Sherlock, P. Sood, T. K. Prakasha, Phosphorus Sulfur Silicon Relat. Elem. 1997, 124-125, 7-22, and references cited therein.
56. R. Burgada, A. Mohri, Phosphorus Sulfur 1982, 13, 85-95.
57. C. Laurenço, D. Bernard, R. Burgada, C. R. Acad. Sci. Paris, Série C 1974, 278, 1301-1304.
58. [26a] C. Laurenço, R. Burgada, Tetrahedron 1976, 32, 2253-2255.
59. [26b] A. A. Prishchenko, D. A. Pisarnitskii, M. V. Livantsov, V. S. Petrosyan, J. Gen. Chem. USSR 1992, 62, 1772-1773.
60. R. Burgada, H. Germa, C. R. Acad. Sci. Paris, Série C 1968, 267, 270-273.
61. Y. Vannoorenberghe, G. Buono, J. Am. Chem. Soc. 1990, 112, 6142-6143.
62. [29a] M. L. Bojin; S. Barkallah, S. A. Evans, Jr. J. Am. Chem. Soc. 1996, 118, 1549-1550.
63. [29b] S. Kojima, K. Kawaguchi, K. Y. Akiba, Tetrahedron Lett. 1997, 38, 7753-7756.
64. [30a] B. Garrigues, D. Boyer, A. Munoz, Can. J. Chem. 1984, 62, 2170-2178.
65. [30b] B. Garrigues, A. Munoz, Can. J. Chem. 1984, 62, 2179-2185.
66. M. Koenig, A. Munoz, B. Garrigues, R. Wolf, Phosphorus Sulfur 1979, 6, 435-451.
67. B. Garrigues, M. Koenig, A. Munoz, Tetrahedron Lett. 1979, 4205-4208.
68. [33a] A. Munoz, Bull. Soc. Chim. Fr. 1977, 728-736.
69. [33b] A. Munoz, B. Garrigues, M. Koenig, Tetrahedron 1980, 36, 2467-2482.
70. E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds Wiley-Interscience, New York, 1994, pp. 1119, 1138.
71. S. Olagnon-Bourgeot, M. Chastrette, F. Chastrette, D. Wilhelm, Bull. Soc. Chim. Fr. 1997, 134, 5-11.
72. [36a] Z. Glowacki, M. Hoffmann, M. Topolski, J. Rachon, Phosphorus Sulfur Silicon Relat. Elem. 1991, 60, 67-71.
73. [36b] T. G. Appleton, J. R. Hall, A. D. Harris, H. A. Kimlin, I. J. McMahon, Aust. J. Chem. 1984, 37, 1833-1840.
74. [36c] H. Lachmann, K. D. Schnackerz, Org. Magn. Res. 1984, 22, 101-105.
75. [37a] G. Stork, S. R. Dowd, J. Am. Chem. Soc. 1963, 85, 2178-2180.
76. [37b] S. Hammerum, J. Chem. Soc., Perkin Trans. 2 1973, 854-861.
77. R. E. Lutz, P. S. Bailey, R. J. Rowlett, J. W. Wilson, III, R. K. Allison, M. T. Clark, N. H. Leake, R. H. Jordan, R. J. Keller, K. C. Nicodemus, J. Org. Chem. 1947, 12, 760-766.
78. [39a] E. J. Enholm, D. C. Forbes, D. P. Holub, Synth. Commun. 1990, 20, 981-987.
79. [39b] P. Scrimin, P. Tecilla, U. Tonellato, J. Am. Chem. Soc. 1992, 114, 5086-5092.
80. B. L. Emling, R. J. Horvath, A. J. Saraceno, E. F. Ellermeyer, L. Haille, L. D. Hudac, J. Org. Chem. 1959, 24, 657-660.