Synthesis of aminocyclobutanes through ring expansion of N-vinyl-β-lactams

Organic Letters

Volumn 11, Issue 6, 2009, Pages 1281-1284

  Cheung, Lawrence L W ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; CYCLOBUTANE DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

BETA-LACTAMS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOBUTANES; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE;

EID: 64049090447     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900118d     Document Type: Article

References (33)

1. (a) Alcaide, B.; Almendros, P. Synlett 2002, 3, 381.
2. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
3. (c) Alcaide, B.; Almendros, P. Curr. Med. Chem. 2004, 29, 1921.
4. (a) Gilman, H.; Speeter, H. J. Am. Chem. Soc. 1943, 65, 2255.
5. (b) Hart, D. J.; Ha, D. C. Chem. Rev. 1989, 89, 1447.
6. (a) Grai, R. JustusLiebigs Ann. Chem. 1963, 661, 111.
7. (b) Hoffmann, H.; Diehr, H. J. Tetrahedron Lett. 1963, 4, 1875.
8. (c) Friedrich, H. J. Tetrahedron Lett. 1971, 12, 2981.
9. (a) Kinugasa, M.; Hashimoto, S. J. Chem. Soc. Chem. Commun. 1972, 466.
10. (b) Pal, R.; Ghosh, S. C; Chandra, K.; Basak, A. Synlett., 2007, 2321.
11. (a) Staudinger, H Justus Liebigs Ann. Chem. 1907, 356, 51.
12. (b) Palomo, C; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223.
13. (c) France, S.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
14. Rappoport, Z.; Liebman, J. F. The chemistry cyclobutanes; John Wiley and Sons: Chichester, 2005.
15. For utility of aminocyclobutane derivatives in drug discovery, see: Allan, R. D.; Hanrahan, J. R.; Hambley, T. W.; Johnston, G. A. R.; Mewett, K. N.; Mitrovic, A. D. J. Med. Chem. 1990, 33, 2905.
16. Moriconi, E. J.; Meyer, W. C. Tetrahedron Lett. 1968, 35, 3823.
17. Durst, T.; O'Sullivan, M. J. J. Org. Chem. 1970, 35, 2043.
18. (a) Harried, S. S; Lee, C. P.; Yang, G.; Lee, T. I. H.; Myles, D. C. J. Org. Chem. 2003, 68, 6646.
19. (b) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599.
20. (c) Barton, D. H. R.; Bashiardes, G.; Pourrey, J. L. Tetrahedron Lett. 1983, 24, 1605.
21. (d) Blaskovicova, M.; Gaplovsky, A.; Blasko, J. Molecules 2007, 11, 188.
22. (e) Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675.
23. Jiang, L.; Job, G. E.; Klapers, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
24. (a) Chen, P.; Chen, Y.; Carroll, P. J.; Sieburth, S. M. Org. Lett. 2006, 8, 3367.
25. (b) Commins, D. L.; Zheng, X.; Goehring, R. R. Org. Lett. 2002, 4, 1611.
26. (c) Chiba, T.; Takada, Y.; Kaneko, C.; Kiuchi, F.; Tsuda, Y. Chem. Pharm. Bull. 1990, 38, 3317.
27. (d) Chiba, T.; Takada, Y.; Naito, T.; Kaneko, C. Chem. Pharm. Bull. 1990, 38, 2335.
28. (e) Kaneko, C.; Ychiyama, K.; Sato, M.; Katagiri, N. Chem. Pharm. Bull. 1986, 34, 3658.
29. (f) Naito, T.; Kaneko, C. Chem. Pharm. Bull. 1985, 33, 5328.
30. (g) Kaneko, C.; Katagiri, N.; Uchiyama, K.; Yamada, T. Chem. Pharm. Bull. 1985, 33, 4160.
31. (a) Brown, J. M.; Golding, B. T.; Stofko, J. J. J. Chem. Soc, Chem. Commun. 1973, 319b.
32. (b) Vogel, E. Ann. 1958, 615, 1.
33. (c) Alcaide, B.; Rodríguez-Ranera, C.; Rodríguez-Vicente, A. Tetrahedron Lett. 2001, 42, 3081.