Synthesis of c(αα)-unsymmetrically disubstituted nitroesters by electron transfer C-alkylation of ethyl 2-nitropropionate anion

Tetrahedron

Volumn 54, Issue 19, 1998, Pages 4923-4934

  Béraud, Valérie ^a   Perfetti, Patricia ^a   Pfister, Christine ^a   Kaafarani, Mustapha ^a   Vanelle, Patrice ^a   Crozet, Michel P ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; AMINO ACID; ANION; ESTER; ETHYL 2 NITROPROPIONATE; METHACRYLIC ACID DERIVATIVE; NITRO DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BINDING; ELECTRON TRANSPORT; ORGANIC CHEMISTRY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032080274     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00194-X     Document Type: Article

References (82)

1. 1. Shipchandler, M. T. Synthesis 1979, 666-686 and references therein.
2. 2. Diez-Barra, E.; de la Hoz, A.; Moreno, A. Synth. Commun. 1994, 24, 1817-1821.
3. 3. (a) Zen, S.; Kaji, E. Bull. Chem. Soc. Jpn. 1970, 43, 2277 and 1973, 46, 337-338.
4. 3. (a) Zen, S.; Kaji, E. Bull. Chem. Soc. Jpn. 1970, 43, 2277 and 1973, 46, 337-338.
5. (b) Gogte, V. N.; Natu, A. A.; Pore, V. S. Synth. Commun. 1987, 17, 1421-1429.
6. (c) Niyazymbetov, M. E.; Evans, D. H. J. Org. Chem. 1993, 58, 779-783 and references therein.
7. 4 (a) Herz, W.; Toggweiler, U. J. Org. Chem. 1964, 29, 213-214.
8. (b) Heinzelman, R. V.; Anthony, W.C.; Lyttle, D. A.; Szmuskovicz, J. J. Org. Chem. 1960, 25, 1548-1558, Troxler, F. Helv. Chim. Acta 1969, 51, 1214-1224. Black, D. St. C.; Craig, D. C.; Deb-Das, R. B.; Kumar, N.; Wright, T. Austr. J. Chem. 1993, 46, 1725-1742.
9. (b) Heinzelman, R. V.; Anthony, W.C.; Lyttle, D. A.; Szmuskovicz, J. J. Org. Chem. 1960, 25, 1548-1558, Troxler, F. Helv. Chim. Acta 1969, 51, 1214-1224. Black, D. St. C.; Craig, D. C.; Deb-Das, R. B.; Kumar, N.; Wright, T. Austr. J. Chem. 1993, 46, 1725-1742.
10. (b) Heinzelman, R. V.; Anthony, W.C.; Lyttle, D. A.; Szmuskovicz, J. J. Org. Chem. 1960, 25, 1548-1558, Troxler, F. Helv. Chim. Acta 1969, 51, 1214-1224. Black, D. St. C.; Craig, D. C.; Deb-Das, R. B.; Kumar, N.; Wright, T. Austr. J. Chem. 1993, 46, 1725-1742.
11. (c) Bonnet, R.; Brown, R. F. C.; Clark, V. M.; Sutherland, I. O.; Sir Alexander Todd J. Chem. Soc. 1959, 2094-2098.
12. (d) Ono, N.; Miyake, H.; Fujii, M.; Kaji, A. Tetrahedron Lett. 1983, 24, 3477-3480.
13. (e) Martynov, V. F.; Grebenkina, V. M. J. Gen. Chem. USSR (Engl. Transl.) 1968, 38, 999-1001.
14. (f) Swaringen, R. A.; Yeowell, D. A.; Wisowaty, J. C.; El-Sayad, H. A.; Stewart, E. L.; Darnafall, M. E. J. Org. Chem. 1979, 44, 4825-4829.
15. (g) Wynberg, H.; Helder, R. Tetrahedron Lett. 1975, 4057-4060.
16. (h) Saari, W. S. J. Org. Chem. 1967, 32, 4074-4076.
17. (i) Robinson, B.; Shepherd, D. M. J. Chem. Soc. 1961, 5037-5038.
18. (j) Ono, N.; Hamamoto, I.; Kaji, A. Bull. Chem. Soc. Jpn. 1985, 58, 1863-1864.
19. (k) Piotrowska, H.; Wejroch, K. Liebigs Ann. Chem. 1992, 8, 871-876.
20. (l) Ono, N.; Tamura, R.; Kaji, A. J. Am. Chem. Soc. 1983, 105, 4017-4022.
21. (m) Renger, B. Arch. Pharm. (Weinheim Ger.) 1982, 315, 472-473.
22. (n) Laikter, A. L.; Niyazymbetov, M. E.; Evans, D. H.; Samet, A. V.; Semenov, V. V. Tetrahedron Lett. 1993, 34, 4465-4468.
23. (o) Attanasi, O. A.; Ballini, R.; Liao, Z.; Santensanio, S.; Serra-Zanetti, F. Tetrahedron 1993, 49, 7027-7036.
24. (p) Sawamura, M.; Nakayama, Y.; Tang, W.M.; Ito, Y. J. Org. Chem. 1996, 61, 9090-9096.
25. (q) Keller, E.; Feringa, B. L. Synlett 1997, 842-844.
26. 5. Kornblum, N.; Michel, R. E.; Kerber, R. C. J. Am. Chem. Soc. 1966, 88, 5660-5662 and 5662-5663.
27. 6. Russell, G. A.; Danen, W. C. J. Am. Chem. Soc. 1966, 88, 5663-5665.
28. 7 Kim, J. K.; Bunnett, J. F. J. Am. Chem. Soc. 1970, 92, 7463-7464.
29. 3-Carbon. In Photoinduced Electron Transfer, Fox, M. A.; Chanon, M., Eds.; Elsevier: Amsterdam, 1988, Part C, chap. 4.8, pp. 421-486.
30. (b) Kornblum, N. Aldrichim. Acta 1990, 23, 71-78.
31. (c) Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, 2-130.
32. RN1 Reaction of Organic Halides. In The Chemistry of Functional Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Suppl. D2, chap. 24, pp 1395-1485.
33. RN1 Reaction of Organic Halides. In The Chemistry of Functional Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Suppl. D2, chap. 24, pp 1395-1485.
34. RN1 Reaction of Organic Halides. In The Chemistry of Functional Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Suppl. D2, chap. 24, pp 1395-1485.
35. 9. (a) Vanelle, P.; Crozet, M. P.; Maldonado, J.; Barreau, M. Eur. J. Med. Chem. 1991, 26, 167-178.
36. (b) Jentzer, O.; Vanelle, P.; Crozet, M. P.; Maldonado, J.; Barreau, M. Eur. J. Med. Chem. 1991, 26, 687-697.
37. (c) Crozet, M. P.; Gellis, A., Pasquier, C.; Vanelle, P.; Aune, J.-P. Tetrahedron Lett. 1995, 36, 525-528.
38. (d) Roubaud, C.; Vanelle, P.; Maldonado, J.; Crozet, M. P. Tetrahedron 1995, 51, 9643-9656.
39. (e) Vanelle, P.; Benakli, K.; Maldonado, J.; Roubaud, C.; Crozet, M. P. Heterocycles 1996, 43, 731-735.
40. (f) Gellis, A.; Vanelle, P.; Maldonado, J.; Crozet, M. P. Tetrahedron Lett. 1997, 38, 2085-2086.
41. (g) Gellis, A.; Vanelle, P.; Kaafarani, M.; Benakli, K.; Crozet, M. P. Tetrahedron 1997, 53, 5471-5484.
42. 10. (a) Kornblum, N.; Boyd, S. D.; Stuchal, F. W. J. Am. Chem. Soc. 1970, 92, 5783-5784.
43. (b) Kornblum, N.; Boyd, S. D. J. Am. Chem. Soc. 1970, 92, 5784-5785.
44. (c) Russell, G. A.; Norris, R. K.; Panek, E. J. J. Am. Chem. Soc. 1971, 93, 5839-5845.
45. 11. Recent reviews concerning α,α-disubstituted α-amino acids: (a) Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264.
46. (b) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917.
47. (c) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16.
48. (d) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
49. (e) Ojima, I. Acc. Chem. Res. 1995, 28, 383-389.
50. (f) Schoemaker, H. E.; Boesten, W. H. J.; Kaptein, B.; Roos, E. C.; Broxterman, Q. B. ; van den Tweel, W. J. J.; Kamphuis, J. Acta Chem. Scand. 1996, 50, 225-233.
51. (g) Ohfune, Y.; Moon, S.-H.; Horikawa, M. Pure Appl. Chem. 1996, 68, 645-648.
52. (h) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748.
53. (i) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
54. Recent articles concerning α,α-disubstituted α-amino acids: (a) Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405-7406 and references therein.
55. (b) Sawamura, M.; Nakayama, Y.; Tang, W.-M.; Ito, Y. J. Org. Chem. 1996, 61, 9090-9096 and references therein.
56. (c) Scott, W. L.; Zhou, C.; Fang, Z.; O'Donnell, M. J. Tetrahedron Lett. 1997, 38, 3695-3698.
57. 12. Kornblum, N.; Blackwood, R. K.; Powers, J. W. J. Am. Chem. Soc. 1957, 79, 2507-2509.
58. 13. (a) Vanelle, P.; Maldonado, J.; Madadi, N.; Gueiffier, A.; Teulade, J.-C.; Chapat, J.-P.; Crozet, M. P. Tetrahedron Lett. 1990, 31, 3013-3016.
59. (b) Vanelle, P.; Madadi, N.; Roubaud C.; Maldonado, J.; Crozet, M. P. Tetrahedron 1991, 47, 5173-5184.
60. (c) Crozet, M. P.; Surzur, J.-M.; Vanelle, P.; Ghiglione, C.; Maldonado, J. Tetrahedron Lett. 1985, 26, 1023-1026.
61. (d) Crozet, M. P.; Giraud, L.; Sabuco, J.-F.; Vanelle, P.; Barreau, M. Tetrahedron Lett. 1991, 32, 4125-4128.
62. (e) Crozet, M. P.; Jentzer, O.; Vanelle, P. Tetrahedron Lett. 1987, 28, 5531-5534.
63. 14. Ono, N.; Tamura, R.; Eto, H.; Hamamoto, I.; Nakatsuka, T.; Hayami, J.-I.; Kaji, A. J. Org. Chem. 1983, 48, 3678-3684.
64. 15. Jacobs, B. D.; Kwon, S.-J.; Field, L. D.; Norris, R. K.; Randles, D. Wilson, K.; Wright, T. A. Tetrahedron Lett. 1985, 26, 3495-3498.
65. 16. (a) Russell, G. A.; Khanna, R. K. J. Am. Chem. Soc. 1985, 107, 1450-1452; Tetrahedron 1985, 41, 4133-4145.
66. 16. (a) Russell, G. A.; Khanna, R. K. J. Am. Chem. Soc. 1985, 107, 1450-1452; Tetrahedron 1985, 41, 4133-4145.
67. (b) Bowmann, W. R.; Golding, B. T.; Watson, W. P. unpublished work.
68. 17. Weisler, L.; Helmkamp, R.W. J. Am. Chem. Soc. 1945, 67, 1167-1171.
69. 18. Russell, G. A. Adv. Phys. Org. Chem. 1987, 23, 271-322.
70. 19. Fossey, J.; Lefort, D.; Sorba, J. Réactivité des Radicaux. In Les Radicaux Libres en Chimie Organique, Masson: Paris, 1993, chap. 6, pp. 68-91.
71. 20. Chanon, M.; Tobe, M. L. Angew. Chem. Int. Ed. Engl. 1982, 21, 1-23.
72. 21. Brown, T. M.; Cooksey, C. J.; Crich, D.; Dronsfield, A. T.; Ellis, R. J. Chem. Soc. Perkin Trans. 1 1993, 2131-2136.
73. 22. (a) Kornblum, N.; Eicher, J. H. J. Am. Chem. Soc. 1956, 78, 1494-1497.
74. (b) Armand, J.; Guetté, J.-P. Bull. Soc. Chim. Fr. 1969, 2894-2900.
75. (c) Syed Masarrat, A.; Yoshihiko, M.; Shigeo, T. Synthesis 1988, 805-806.
76. 23. The authors thank Professor Dennis H. Evans for private discussion on the mechanism of the electrochemical C-alkylation of ethyl 2-nitropropionate anion.
77. 24. Ram, S.; Ehrenkauf, R. E. Tetrahedron Lett. 1984, 25, 3415-3418.
78. 25. Saari, W. S.; Williams, J.; Britcher, S. F.; Wolf, D. E.; Kuehl, Jr., F. A. J. Med. Chem. 1967, 10, 1008-1014.
79. 26. (a) Nair, M. N.; Nagarajan, K. Nitroimidazoles as Chemotherapeutic Agents in Progress in Drug Research; Jücker, E., Ed.; Birkhaüser Verlag: Basel, 1983, Vol. 27, pp 163-252.
80. (b) Al-Shaar, A. H. M.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, C. A. J. Chem. Soc. Perkin Trans I 1992, 2779-2788.
81. 27. For examples of lactonization: (a) Smith, I. L.; Austin, F. L. J. Am. Chem. Soc. 1942, 64, 528-533.
82. (b) Hillery, P. S.; Cohen, L. A. J. Org. Chem. 1983, 48, 3465-3471.