Conjugate addition to 1-phosphono-2-aza-1,3-butadienes: Synthesis of phosphonylated γ-lactams

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 191-198

  Vanderhoydonck, Bart ^a   Stevens, Christian V ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; HALOGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

HALOGENATED PHENYL SUBSTITUENTS; NUCLEOPHILES; REGIOSELECTIVITY; SODIUM MALONATE;

OLEFINS;

1 [(2 BROMOPHENYL)(DIETHOXYPHOSPHORYL)METHYL] 4,4 DIMETHYL 2 OXO 3 PYRROLIDINECARBOXYLATE; 1 [(2 CHLOROPHENYL)(DIETHOXYPHOSPHORYL)METHYL] 4,4 DIMETHYL 2 OXO 3 PYRROLIDINECARBOXYLATE; 1 [(4 BROMOPHENYL)(DIETHOXYPHOSPHORYL)METHYL] 4,4 DIMETHYL 2 OXO 3 PYRROLIDINECARBOXYLATE; 1 [(DIETHOXYPHOSPHORYL)(2 FLUOROPHENYL)METHYL] 4,4 DIMETHYL 2 OXO 3 PYRROLIDINECARBOXYLATE; 1 [(DIETHOXYPHOSPHORYL)(4 FLUOROPHENYL)METHYL] 4,4 DIMETHYL 2 OXO 3 PYRROLIDINECARBOXYLATE; 1 [(DIETHOXYPHOSPHORYL)(PHENYL) METHYL] 4,4 DIMETHYL 2 OXO 3 PYRROLIDINECARBOXYLATE; 1 PHOSPHON 2 AZA 1,3 BUTADIENE; 1,3 BUTADIENE; ALKADIENE; AMINE; AZIRIDINE DERIVATIVE; BETA LACTAM; CARBOXYLIC ACID DERIVATIVE; GAMMA LACTAM DERIVATIVE; IMINE; MALONIC ACID; MALONONITRILE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONJUGATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; HALOGENATION; MICHAEL ADDITION; POLARIZATION; POSITION EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SUBSTITUTION REACTION;

AZA COMPOUNDS; BUTADIENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; LACTAMS; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 11844271973     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0488661     Document Type: Article

References (62)

1. For reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (c) Ghosez, L. Stereocontrolled Organic Synthesis; Blackwell: Oxford, 1994; p 193. (d) Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. (e) Boger, D. L. In Comprehensive Organic Synthesis B; Trost, M. B., Paquete, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 451.
2. For reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (c) Ghosez, L. Stereocontrolled Organic Synthesis; Blackwell: Oxford, 1994; p 193. (d) Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. (e) Boger, D. L. In Comprehensive Organic Synthesis B; Trost, M. B., Paquete, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 451.
3. For reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (c) Ghosez, L. Stereocontrolled Organic Synthesis; Blackwell: Oxford, 1994; p 193. (d) Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. (e) Boger, D. L. In Comprehensive Organic Synthesis B; Trost, M. B., Paquete, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 451.
4. For reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (c) Ghosez, L. Stereocontrolled Organic Synthesis; Blackwell: Oxford, 1994; p 193. (d) Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. (e) Boger, D. L. In Comprehensive Organic Synthesis B; Trost, M. B., Paquete, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 451.
5. For reviews, see: (a) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379. (b) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (c) Ghosez, L. Stereocontrolled Organic Synthesis; Blackwell: Oxford, 1994; p 193. (d) Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. (e) Boger, D. L. In Comprehensive Organic Synthesis B; Trost, M. B., Paquete, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 451.
6. For recent papers, see: (a) Alves, M. J.; Durães, M. M.; Gil Fortes, A. Tetrahedron Lett. 2003, 44, 5079. (b) Ntirampebura, D.; Ghosez, L. Synthesis 2002, 2043. (c) Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941.
7. For recent papers, see: (a) Alves, M. J.; Durães, M. M.; Gil Fortes, A. Tetrahedron Lett. 2003, 44, 5079. (b) Ntirampebura, D.; Ghosez, L. Synthesis 2002, 2043. (c) Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941.
8. For recent papers, see: (a) Alves, M. J.; Durães, M. M.; Gil Fortes, A. Tetrahedron Lett. 2003, 44, 5079. (b) Ntirampebura, D.; Ghosez, L. Synthesis 2002, 2043. (c) Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941.
9. For recent papers, see: (a) Palacios, F.; Alonso, C.; Rubiales, G.; Tobillas, C.; Ezpeleta, J. M. Heterocycles 2003, 61, 493. (b) Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. J. Org. Chem. 2002, 67, 1941. (c) Venturini, A.; Joglar, J.; Fustero, S.; Gonzalez, J. J. Org. Chem. 1997, 62, 3919.
10. For recent papers, see: (a) Palacios, F.; Alonso, C.; Rubiales, G.; Tobillas, C.; Ezpeleta, J. M. Heterocycles 2003, 61, 493. (b) Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. J. Org. Chem. 2002, 67, 1941. (c) Venturini, A.; Joglar, J.; Fustero, S.; Gonzalez, J. J. Org. Chem. 1997, 62, 3919.
11. For recent papers, see: (a) Palacios, F.; Alonso, C.; Rubiales, G.; Tobillas, C.; Ezpeleta, J. M. Heterocycles 2003, 61, 493. (b) Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. J. Org. Chem. 2002, 67, 1941. (c) Venturini, A.; Joglar, J.; Fustero, S.; Gonzalez, J. J. Org. Chem. 1997, 62, 3919.
12. For recent papers, see: (a) Palacios, F.; Herrán, E.; Rubiales, G.; Ezpeleta, J. M. J. Org. Chem. 2002, 67, 2131. (b) Palacios, F.; Herrán, E.; Rubiales, G. J. Org. Chem. 1999, 64, 6239. (c) Pinho e Melo, T. M. V. D.; Fausto, R.; d'A Rocha Gonsalves, A. M.; Gilchrist, T. L. J. Org. Chem. 1998, 63, 5350.
13. For recent papers, see: (a) Palacios, F.; Herrán, E.; Rubiales, G.; Ezpeleta, J. M. J. Org. Chem. 2002, 67, 2131. (b) Palacios, F.; Herrán, E.; Rubiales, G. J. Org. Chem. 1999, 64, 6239. (c) Pinho e Melo, T. M. V. D.; Fausto, R.; d'A Rocha Gonsalves, A. M.; Gilchrist, T. L. J. Org. Chem. 1998, 63, 5350.
14. For recent papers, see: (a) Palacios, F.; Herrán, E.; Rubiales, G.; Ezpeleta, J. M. J. Org. Chem. 2002, 67, 2131. (b) Palacios, F.; Herrán, E.; Rubiales, G. J. Org. Chem. 1999, 64, 6239. (c) Pinho e Melo, T. M. V. D.; Fausto, R.; d'A Rocha Gonsalves, A. M.; Gilchrist, T. L. J. Org. Chem. 1998, 63, 5350.
15. Kukhar, V. P.; Hudson, H. R. Aminophosphonic and Aminophosphinic Acids, Chemistry and Biological Activity; John Wiley & Sons, Ltd.: New York, 2000.
16. (a) Frick, L.; Wolfenden, R. In Design of Enzyme Inhibitors as Drugs; Sandler, M., Smith, H. J., Eds.; Oxford University Press: Oxford, 1989; p 19.
17. (b) Kafarski, P.; Lejczak, B. Phosphorous, Sulfur Silicon Relat. Elem. 1991, 63, 193.
18. Smith, A. B.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879.
19. (a) Cristau, H.-J.; Coulombeau, A.; Genevois-Borella, A.; Pirat, J.-L. Tetrahedron Lett. 2001, 42, 4491.
20. (b) Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604.
21. (c) Wallace, E. M.; Moliterni, J. A.; Moskal, M. A.; Neubert, A. D., Marcopoulos, N.; Stamford, L. B.; Trapani, A. J.; Savage, P.; Chou, M.; Jeng, A. Y. J. Med. Chem. 1998, 41, 1513.
22. (d) Wang, C.-L. J.; Taylor, T. L.; Mical, A. J.; Spitz, S.; Reilly, T. M. Tetrahedron Lett. 1992, 33, 7667.
23. (e) Pratt, R. F. Science 1989, 246, 917.
24. Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600.
25. (a) Falorni, M.; Porcheddu, A.; Giacomelli, G. Tetrahedron: Asymmetry 1997, 8, 1633.
26. (b) Hamilton, G. S.; Huang, Z.; Yang, X.-J.; Patch, R. J.; Narayanan, B. A.; Ferkany, J. W. J. Org. Chem. 1993, 55, 7263.
27. Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234.
28. Rawls, R. L. Chem. Eng. News 1939, 17, 38.
29. (a) Vanderhoydonck, B.; Stevens, C. V. Synthesis 2004, 722.
30. (b) Stevens, C. V.; Gallant, M.; De Kimpe, N. Tetrahedron Lett. 1999, 40, 3457.
31. (a) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; Rodríguez, M.; Pagalday, J. Tetrahedron 2003, 59, 2617.
32. (b) Palacios, F.; Gil, M. J.; Martínez de Marigorta, E.; Rodríguez, M. Tetrahedron 2000, 56, 6319.
33. (c) Palacios, F.; Gil, M. J.; Martínez de Marigorta, E.; Rodríguez, M. Tetrahedron Lett. 1999, 40, 2411.
34. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1996, 52, 4857.
35. Gérard, S.; Dive, G.; Clamot, B.; Touillaux, R.; Marchand-Brynaert, J. Tetrahedron 2002, 58, 2423.
36. Ogilvie, W. W.; Yoakim, C.; Dô, F.; Haché, B.; Lagacé, L.; Naud, J.; O'Meara, J. A.; Déziel, R. Bioorg. Med. Chem. 1999, 7, 1521.
37. (a) Koster, W. H.; Zahler, R.; Chang, H. W.; Cimarusti, C. M.; Jacobs, G. A.; Perri, M. J. Am. Chem. Soc. 1983, 105, 3743.
38. (b) Shiozaki, M.; Masuko, H. Heterocycles 1984, 22, 1727.
39. (c) Campbell, M. M.; Carruthers, N. I.; Mickel, S. J. Tetrahedron 1982, 38, 2513.
40. (a) Darling, S. D.; Muralidharan, F. N.; Muralidharan, V. B. Tetrahedron Lett. 1979, 30, 2757.
41. (b) Darling, S. D.; Muralidharan, F. N.; Muralidharan, V. B. Tetrahedron Lett. 1979, 30, 2761.
42. (c) Pudovik, A. N.; Konovalova, I. V.; Ishmaeva, E. A. Zh. Obshch. Khim. 1962, 32, 237; Chem. Abstr. 1962, 57, 15146a.
43. (c) Pudovik, A. N.; Konovalova, I. V.; Ishmaeva, E. A. Zh. Obshch. Khim. 1962, 32, 237; Chem. Abstr. 1962, 57, 15146a.
44. Ojea, V.; Conde, S.; Ruiz, M.; Fernández, M. C.; Quintela, J. M. Tetrahedron Lett. 1997, 38, 4311.
45. Nozaki, Y.; Katayama, N.; Ono, H.; Tsubotani, S.; Harada, S.; Okazaki, H.; Nakao, Y. Nature 1987, 325, 179.
46. For some examples, see: (a) Kar, G. K.; Roy, B. C.; Adhikari, S. D.; Ray, J. K.; Brahma, N. K. Bioorg. Med. Chem. 1998, 6, 2397. (b) Allen, N. E.; Boyd, D. B.; Campbell, J. B.; Deeter, J. B.; Elzey, T. K.; Foster, B. J.; Hatfield, L. D.; Hobbs, J. N., Jr.; Hornback, W. J.; Hunden, D. C.; Jones, N. D.; Kinnick, M. D.; Morin, J. M., Jr.; Munroe, J. E.; Swartzendruber, J. K.; Vogt, D. G. Tetrahedron 1989, 45, 1905. (c) Jungheim, L. N.; Sigmund, S. K. J. Org. Chem. 1987, 52, 4007.
47. For some examples, see: (a) Kar, G. K.; Roy, B. C.; Adhikari, S. D.; Ray, J. K.; Brahma, N. K. Bioorg. Med. Chem. 1998, 6, 2397. (b) Allen, N. E.; Boyd, D. B.; Campbell, J. B.; Deeter, J. B.; Elzey, T. K.; Foster, B. J.; Hatfield, L. D.; Hobbs, J. N., Jr.; Hornback, W. J.; Hunden, D. C.; Jones, N. D.; Kinnick, M. D.; Morin, J. M., Jr.; Munroe, J. E.; Swartzendruber, J. K.; Vogt, D. G. Tetrahedron 1989, 45, 1905. (c) Jungheim, L. N.; Sigmund, S. K. J. Org. Chem. 1987, 52, 4007.
48. For some examples, see: (a) Kar, G. K.; Roy, B. C.; Adhikari, S. D.; Ray, J. K.; Brahma, N. K. Bioorg. Med. Chem. 1998, 6, 2397. (b) Allen, N. E.; Boyd, D. B.; Campbell, J. B.; Deeter, J. B.; Elzey, T. K.; Foster, B. J.; Hatfield, L. D.; Hobbs, J. N., Jr.; Hornback, W. J.; Hunden, D. C.; Jones, N. D.; Kinnick, M. D.; Morin, J. M., Jr.; Munroe, J. E.; Swartzendruber, J. K.; Vogt, D. G. Tetrahedron 1989, 45, 1905. (c) Jungheim, L. N.; Sigmund, S. K. J. Org. Chem. 1987, 52, 4007.
49. For some examples, see: (a) Crossley, M. J.; Crumbie, R. L.; Fung, Y. M.; Potter, J. J.; Pegler, M. A. Tetrahedron Lett. 1987, 28, 2883. (b) Boyd, D. B.; Elzey, T. K.; Hatfield, L. D.; Kinnick, M. D.; Morin, J. M., Jr. Tetrahedron Lett. 1986, 27, 3453. (c) Boyd, D. B.; Foster, B. J.; Hatfield, L. D.; Hornback, W. J.; Jones, N. D.; Munroe, J. E.; Swartzendruber, J. K. Tetrahedron Lett. 1986, 27, 3457. (d) Baldwin, J. E.; Lowe, C.; Schofield, C. J. Tetrahedron Lett. 1986, 27, 3461.
50. For some examples, see: (a) Crossley, M. J.; Crumbie, R. L.; Fung, Y. M.; Potter, J. J.; Pegler, M. A. Tetrahedron Lett. 1987, 28, 2883. (b) Boyd, D. B.; Elzey, T. K.; Hatfield, L. D.; Kinnick, M. D.; Morin, J. M., Jr. Tetrahedron Lett. 1986, 27, 3453. (c) Boyd, D. B.; Foster, B. J.; Hatfield, L. D.; Hornback, W. J.; Jones, N. D.; Munroe, J. E.; Swartzendruber, J. K. Tetrahedron Lett. 1986, 27, 3457. (d) Baldwin, J. E.; Lowe, C.; Schofield, C. J. Tetrahedron Lett. 1986, 27, 3461.
51. For some examples, see: (a) Crossley, M. J.; Crumbie, R. L.; Fung, Y. M.; Potter, J. J.; Pegler, M. A. Tetrahedron Lett. 1987, 28, 2883. (b) Boyd, D. B.; Elzey, T. K.; Hatfield, L. D.; Kinnick, M. D.; Morin, J. M., Jr. Tetrahedron Lett. 1986, 27, 3453. (c) Boyd, D. B.; Foster, B. J.; Hatfield, L. D.; Hornback, W. J.; Jones, N. D.; Munroe, J. E.; Swartzendruber, J. K. Tetrahedron Lett. 1986, 27, 3457. (d) Baldwin, J. E.; Lowe, C.; Schofield, C. J. Tetrahedron Lett. 1986, 27, 3461.
52. For some examples, see: (a) Crossley, M. J.; Crumbie, R. L.; Fung, Y. M.; Potter, J. J.; Pegler, M. A. Tetrahedron Lett. 1987, 28, 2883. (b) Boyd, D. B.; Elzey, T. K.; Hatfield, L. D.; Kinnick, M. D.; Morin, J. M., Jr. Tetrahedron Lett. 1986, 27, 3453. (c) Boyd, D. B.; Foster, B. J.; Hatfield, L. D.; Hornback, W. J.; Jones, N. D.; Munroe, J. E.; Swartzendruber, J. K. Tetrahedron Lett. 1986, 27, 3457. (d) Baldwin, J. E.; Lowe, C.; Schofield, C. J. Tetrahedron Lett. 1986, 27, 3461.
53. Hungate, R. W.; Chen, J. L.; Starbuck, K. E.; Vacca, J. P.; McDaniel, S. L.; Levin, R. B.; Dorsey, B. D.; Guare, J. P.; Holloway, M. K.; Whitter, W.; Darke, P. L.; Zugay, J. A.; Schleif, W. A.; Emini, E. A.; Quintero, J. C.; Lin, J. H.; Chen, I.-W.; Anderson, P. S.; Huff, J. R. Bioorg. Med. Chem. 1994, 2, 859.
54. Dugar, S.; Kirkup, M. P.; Clader, J. W.; Lin, S.-I.; Rizvi, R.; Snow, M. E.; Davis, H. R., Jr.; McCombie, S. W. Bioorg. Med. Chem. Lett. 1995, 5, 2947.
55. (a) Olive, G.; Le Moigne, F.; Mercier, A.; Tordo, P. Synth. Commun. 2000, 30, 619.
56. (b) Uryupin, A. B.; Rakhov, I. A.; Kolesova, V. A.; Petrovskii, P. V.; Mastryukova, T. A.; Kabachnik, M. I. Izv. Akad. Nauk, Ser. Khim. 1995, 2250; Chem. Abstr. 1996, 124, 317320m.
57. (b) Uryupin, A. B.; Rakhov, I. A.; Kolesova, V. A.; Petrovskii, P. V.; Mastryukova, T. A.; Kabachnik, M. I. Izv. Akad. Nauk, Ser. Khim. 1995, 2250; Chem. Abstr. 1996, 124, 317320m.
58. (c) Yamaguchi, M.; Tsukamoto, Y.; Hayashi, A.; Minami, T. Tetrahedron Lett. 1990, 31, 2423.
59. (d) Mikroyannidis, J. A. Phosphorus Sulfur Relat. Elem. 1982, 12, 249.
60. (e) Du, Y.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5709 and references therein.
61. (a) Ross, N. A.; MacGregor, R. R.; Bartsch, R. A. Tetrahedron 2004, 60, 2035.
62. (b) For a review, see: Hart, D. J.; Ha, D. Chem. Rev. 1989, 89, 1447.