Novel synthesis of carbapenam by intramolecular attack of lactam nitrogen toward η1-allenyl and η3-propargylpalladium complex

Journal of Organic Chemistry

Volumn 68, Issue 21, 2003, Pages 8068-8074

  Kozawa, Yuji ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR ATTACK;

COMPLEXATION; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

NITROGEN;

ANTIBIOTIC AGENT; CARBAPENEM DERIVATIVE; ETA1 ALLENYLPALLADIUM; ETA3 PROPARGYLPALLADIUM; LACTAM; NITROGEN ACID DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; WARMING;

CARBAPENEMS; CATALYSIS; CYCLIZATION; LACTAMS; LIGANDS; MOLECULAR STRUCTURE; NITROGEN; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PARGYLINE;

EID: 0142121808     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030123c     Document Type: Article

References (46)

1. (a) Kahan, J. S.; Kahan, F. M.; Goegelman, R.; Currie, S. A.; Jackson, M.; Stapley, E. O.; Miller, T. W.; Miller, A. K.; Hendlin, D.; Mochales, S.; Hernandez, S.; Woodruff, H. B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
2. (b) Albers-Schönberg, G.; Arison, B. H.; Hensens, O. D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E. A.; Rhodes, R. E.; Kahan, J. S.; Kahan, F. M.; Ratcliffe, R. W.; Walton, E.; Ruswinkle, L. J.; Morin, R. B.; Christensen, B. G. J. Am. Chem. Soc. 1978, 100, 6491.
3. (c) Sunagawa, M.; Sasaki, A. Heterocycles 2001, 54, 497.
4. Berks, A. H. Tetrahedron 1996, 52, 331.
5. Barrett, A. G. M.; Sturgess, M. A. Tetrahedron 1988, 44, 5615.
6. (a) Ratcliffe, R. W.; Salzmann, T. N.; Christensen, B. G. Tetrahedron Lett. 1980, 21, 31.
7. (b) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.
8. (c) Williams, M. A.; Hsiao, C.-N.; Miller, M. J. J. Org. Chem. 1991, 56, 2688.
9. (d) Kume, M.; Kubota, T.; Iso, Y. Tetrahedron Lett. 1995, 36, 8043.
10. Trost, B. M.; Chen, S.-F. J. Am. Chem. Soc. 1986, 108, 6053.
11. (a) Roland, S.; Durand, J. O.; Savignac, M.; Genêt, J. P. Tetrahedron Lett. 1995, 36, 3007.
12. (b) Galland, J.-C.; Roland, S.; Malpart, J.; Savignac, M.; Genet, J.-P. Eur. J. Org. Chem. 1999, 621.
13. (c) Duboc, R.; Hénaut, C.; Savignac, M.; Genet, J.-P.; Bhatnagar, N. Tetrahedron Lett. 2001, 42, 2461.
14. (a) Mori, M.; Kozawa, Y.; Nishida, M.; Kanamaru, M.; Onozuka, K.; Takimoto, M. Org, Lett. 2000, 2, 3245.
15. (b) Preliminary report of this article: Kozawa, Y.; Mori, M. Tetrahedron Lett, 2001, 42, 4869,
16. (c) Kozawa, Y.; Mori, M, Tetrahedron Lett. 2002, 43, 111.
17. (a) Hartwig, J, F. Angew. Chem., Int. Ed, 1998, 37, 2046.
18. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
19. (c) Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
20. (d) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
21. (e) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232.
22. (f) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
23. (g) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367.
24. (h) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264.
25. (i) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
26. (j) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.
27. (k) Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35.
28. (l) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
29. (m) Shakespeare, W. C. Tetrahedron Lett. 1999, 40, 2035.
30. (a) Madar, D. J.; Kopecka, H.; Pireh, D.; Pease, J.; Pliushchev, M.; Sciotti, R. J.; Wiedeman, P. E.; Djuric, S. W. Tetrahedron Lett. 2001, 42, 3681.
31. (b) Cacchi, S.; Antonella Goggiamani, G. F.; Zappia, G. Org. Lett. 2001, 3, 2539.
32. (c) He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.
33. (d) Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028.
34. (e) Wagaw, S.; Rennnels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451.
35. Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. 1995, 34, 2589.
36. Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963.
37. Imuta, M.; Itani, H.; Ona, H.; Hamada, Y.; Uyeo, S.; Yoshida, T. Chem. Pharm. Bull. 1991, 39, 663.
38. The coupling constant J between 1- and 2-positions of 41-2α having the 2α-benzoyloxy group is 0 Hz. On the other hand, the coupling constant J between the 1- and 2-positions of 41-2β having the 2β-benzoyloxy group is 5.9 Hz. The fact that the coupling constant J between the 1- and 2-position of 22 was 0 Hz indicates that the silyloxy group was placed at the α-position.
39. (a) Tsutsumi, K.; Ogoshi, S.; Nishiguchi, S.; Kurosawa, H. J. Am. Chem. Soc. 1998, 120, 1938.
40. (b) Tsutsumi, K.; Kawase, T.; Kakiuchi, K.; Ogoshi, S.; Okada, Y.; Kurosawa, H. Bull. Chem. Soc. Jpn. 1999, 72, 2687.
41. (a) Minami, I.; Yuhara, M.; Tsuji, J. Tetrahedron Lett. 1987, 28, 629.
42. (b) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553.
43. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025.
44. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527.
45. (e) Yoshida, M.; Ihara, M. Angew. Chem., Int. Ed. 2001, 40, 616.
46. (f) Yoshida, M.; Fujita, M.; Ishii, T.; Ihara, M. J. Am. Chem. Soc. 2003, 125, 4874.